DOCSLIB.ORG

Study of the Anomalous Thermochemical Behavior of 1,2-Diazines by Correlation-Gas Chromatography

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Study of the Anomalous Thermochemical Behavior of 1,2-Diazines by Correlation-Gas Chromatography 1628 J. Chem. Eng. Data 2010, 55, 1628–1635 Study of the Anomalous Thermochemical Behavior of 1,2-Diazines by Correlation-Gas Chromatography Dmitry Lipkind and James S. Chickos* Department of Chemistry and Biochemistry, University of MissourisSt. Louis, St. Louis, Missouri 63121 Joel F. Liebman Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, Maryland 21250 The vaporization enthalpies and liquid vapor pressures of quinoxaline, quinazoline, phthalazine, benzo[c]cinnoline, 1,10-phenanthroline, phenazine, and triphenylamine are measured by correlation-gas chromatography and compared to values calculated from available literature vaporization, sublimation, and fusion enthalpy data. Good agreement with the literature is observed for all compounds except the 1,2-diazines and the sublimation enthalpy of triphenylamine. The results suggest that liquid 1,2-diazines exhibit an additional intermolecular stabilizing interaction of approximately 6 kJ · mol-1 not present in other diazine isomers. Introduction tion enthalpies and liquid vapor pressures. The standards are injected simultaneously with the target substances. Since each Derivatives of pyrazine, pyrimidine, and pyridazine comprise analyte moves on the column according to its vapor pressure a set of diverse compounds, many of which are found in natural on the column, measurement of the temperature dependence of products and biological systems. Recently we examined the its retention time provides a convenient measure of both its - vaporization enthalpies of the parent compounds by correlation volatility and interaction with the column. Since the vapor gas chromatography and observed that compounds that served pressure of each analyte is inversely proportional to its retention as suitable standards for pyrazines, pyrimidines, and 1,3,5- time, a plot of ln(ta/to)vs1/T, usually over a T ) 30 K range, triazines were unsuitable for use with pyridazines. Upon closer results in a linear relationship with a slope equal to the enthalpy examination of their vaporization enthalpies, it was observed of transfer of the analyte from the column to the gas phase, that intermolecular interactions occurring in pyridazines are g ∆sln Hm(T), divided by the gas constant. The term to refers to a considerably stronger than those in the corresponding pyrim- reference time, 1 min, and ta is the time each analyte spends on idines and pyrazines. The origin of this enhanced intermolecular the column. It is evaluated as the difference between the 1,2 interaction was attributed to the presence of a 1,2-diazine. measured retention time of each analyte and that of a nonretained This article reports the results of a study aimed at: (1) reference. The enthalpy of transfer can be related to the determining whether this enhanced intermolecular interaction following thermodynamic relationship is characteristic of all aromatic 1,2-diazines and (2) evaluating g ) g + g the magnitude of this interaction. The compounds evaluated in ∆sln Hm(Tm) ∆1 Hm(Tm) ∆sln Hm(Tm) (1) g this study include quinoxaline, quinazoline, phthalazine, ben- where ∆l Hm(Tm) refers to the vaporization enthalpy and zo[c]cinnoline, phenazine, and 1,10-phenanthroline. The struc- ∆slnHm(Tm) refers to the interaction of each analyte with the ture of the compounds studied and those used as standards are column measured at some mean temperature, Tm. The enthalpy g illustrated in Figure 1. In the process of identifying additional of transfer, ∆sln Hm(Tm), has been found to correlate linearly g 3 standards that could be useful in correlation gas chromatography with ∆l Hm(T). Temperature T usually differs from Tm. The experiments, the vaporization enthalpy of triphenylamine was quality of the correlation obtained is determined by both also investigated. The sublimation,5 vaporization,6 and fusion7 the quality of data available for the standards and selection of enthalpies of triphenylamine have previously been reported. Our the appropriate standards. initial inclination was to use triphenylamine as one of the The appropriateness of the standards used for the compounds standards in this study, but upon closer inspection, one (or more) studied in this work with the exception of the aromatic 1,2- of these reported measurements appeared to be thermodynami- diazines has previously been demonstrated.1,4 The difference cally incompatible with the others. Correlation-gas chroma- betweenthevaporizationenthalpyvaluemeasuredbycorrelation-gas tography experiments were performed to identify the discordant chromatography and that obtained by other methods was chosen property. as a means of identifying and quantifying the magnitude of this Correlation-gas chromatography is a simple and reliable additional stabilizing interaction found in the liquid phase of method for evaluating vaporization enthalpy and vapor pressure aromatic 1,2-diazines. Pyridazine is the only liquid aromatic 8 regardless of whether the target substance is a solid or liquid.3,4 1,2-diazine whose vaporization enthalpy has been measured. The method requires the use of standards with reliable vaporiza- However, the sublimation and fusion enthalpy of several crystalline aromatic heterocyclic 1,2-diazines have been mea- * Corresponding author. E-mail: [email protected]. sured. A summary of these results is reported in Table 1. 10.1021/je900702t 2010 American Chemical Society Published on Web 12/17/2009 Journal of Chemical & Engineering Data, Vol. 55, No. 4, 2010 1629 Figure 1. Compounds evaluated in this study. From left to right, top to bottom: quinoxaline, quinazoline phthalazine, benzo[c]cinnoline, phenazine, 1,10- phenanthroline, and triphenylamine. Standards: 2,6-dimethylquinoline, 2-phenylpyridine, 4,7-phenanthroline, 7,8-benzoquinoline, acridine, and tributylamine. Table 1. Summary of the (A) Sublimation, Vaporization, and Fusion Enthalpies Available in the Literature and (B) the Vaporization Enthalpy of Triphenylamine and Their Adjustment to T ) 298.15 K g g l l g ∆cr Hm(Tm) Tm ∆cr Hm(298 K) ∆cr Hm(Tfus) Tfus Cp(l)/Cp(cr) ∆cr Hm(298 K) ∆l Hm(298 K) (A) (kJ · mol-1) K (kJ · mol-1) (kJ · mol-1)K(J· mol-1 · K) (kJ · mol-1) (kJ · mol-1) phthalazine 81.1 ( 0.4a 13.3 ( 0.6a 364.5 202.8/149.8 10.7 ( 1.1 70.4 ( 1.2 82.3 ( 2.3b 10.7 ( 1.1 71.6 ( 2.5 96.7c na 96.7 10.7 ( 1.1 86.0 quinoxaline 69.4 ( 0.6a 11.8 ( 0.1a 305.7 202.8/149.8 11.5 ( 0.1 57.9 ( 2.0 66.6 ( 2.0b 11.5 ( 0.1 55.1 ( 2.0 quinazoline 77.6 ( 0.5a 17.0 ( 0.2a 320.9 202.8/149.8 16.0 ( 0.4 61.6 ( 0.6 76.6 ( 1.4b 16.0 ( 0.4 60.6 ( 1.5 phenazine 92.7 ( 0.4d 354 95.1 ( 0.8 20.9 ( 0.7g 447.9 277/201.7 13.2 ( 2.6 81.9 ( 2.7 18.9 ( 0.1d 447.9 11.2 ( 2.6 83.9 ( 2.7 91.8 ( 2.1e 298 91.8 ( 2.1 20.9 ( 0.7g 447.9 13.2 ( 2.6 78.6 ( 3.4 18.9 ( 0.1d 447.9 11.2 ( 2.6 80.6 ( 3.4 90.4 ( 2.5f 298 90.4 ( 2.5 20.9 ( 0.7g 447.9 13.2 ( 2.6 77.2 ( 3.6 18.9 ( 0.1d 447.9 11.2 ( 2.6 79.2 ( 3.6 90.4 ( 1.7g 302 90.4 ( 1.7 20.9 ( 0.7g 447.9 13.2 ( 2.6 77.4 ( 3.1 18.9 ( 0.1d 447.9 11.2 ( 2.6 79.2 ( 3.1 benzo[c]cinnoline 101.7 ( 0.2h 340 103.5 ( 0.6 20.9 ( 0.1h 430 277/201.7 14.1 ( 2.2 89.2 ( 2.3 113.0c na 14.1 ( 2.2 98.9 1,10-phenanthroline 98.3c na 11.8 ( 0.1i 391.1 277/201.7 7.0 ( 1.6 91.3 4,7-phenanthroline 80.8 ( 4.8m triphenylamine 87.9 ( 1.3j 348 90.9 ( 1.6 24.9 ( 0.4k 400.2 394.9/319.5 18.3 ( 2.2 73.7 ( 2.7 g g l l g ∆l Hm(Tm) Tm ∆l Hm(298 K) ∆cr Hm(Tfus) Tfus Cp(l)/Cp(cr) ∆cr Hm(298 K) ∆cr Hm(298 K) (B) (kJ · mol-1) K (kJ · mol-1) (kJ · mol-1)K(J· mol-1 · K) (kJ · mol-1) (kJ · mol-1) triphenylamine 67.4l 523 92.8 ( 6 24.9 ( 0.4k 400.2 394.9/319.5 18.3 ( 2.2 111.1 ( 3.6 a Ref 9. b Ref 10. c Ref 11. na in column three: not available. d Ref 12. e Ref 13. f Ref 14. g Ref 15. h Ref 16. i Ref 17. j Ref 5. k Ref 7. l Ref 6. m Ref 4. The second column of Table 1 lists literature sublimation Fusion enthalpies and fusion temperatures are reported in enthalpies evaluated at the mean temperature of measurement. columns 5 and 6. Adjustments of the enthalpies reported in 1630 Journal of Chemical & Engineering Data, Vol. 55, No. 4, 2010 Table 2. Parameters of (A) the Cox Equation Used for Reference, (B) the Wagner Equation, and (C) the Third-Order Polynomial 7 (A) A1 A2*10 Tb range -1 -2 Cox equation Ao T T KK acridine20 2.89594 -0.00111538 6.486 618.059 383 to 637 7,8-benzoquinoline20 2.88454 -0.00111802 6.6824 14.49 373 to 672 (B) Tc pc range a Wagner equation AW BW CW DW K kPa K 2,6-dimethylquinoline21 -8.993312 3.594873 -4.63173 -2.907492 786 3480 337 to 592 ABC range (C) K3 K2 K D K 4 tri-n-butylamine 30767110 -712464.53 -3836.0 10.769 298 to Tb 4 2-phenylpyridine 82334650 -1199538.89 -2988.7 8.899 298 to Tb 4 4,7-phenanthroline 123705710 -1579329.77 -3296.6 8.741 298 to Tb a Tr ) T/Tc.
Load more

Recommended publications
  • Inventory Size (Ml Or G) 103220 Dimethyl Sulfate 77-78-1 500 Ml
    Inventory Bottle Size Number Name CAS# (mL or g) Room # Location 103220 Dimethyl sulfate 77-78-1 500 ml 3222 A-1 Benzonitrile 100-47-0 100ml 3222 A-1 Tin(IV)chloride 1.0 M in DCM 7676-78-8 100ml 3222 A-1 103713 Acetic Anhydride 108-24-7 500ml 3222 A2 103714 Sulfuric acid, fuming 9014-95-7 500g 3222 A2 103723 Phosphorus tribromide 7789-60-8 100g 3222 A2 103724 Trifluoroacetic acid 76-05-1 100g 3222 A2 101342 Succinyl chloride 543-20-4 3222 A2 100069 Chloroacetyl chloride 79-04-9 100ml 3222 A2 10002 Chloroacetyl chloride 79-04-9 100ml 3222 A2 101134 Acetyl chloride 75-36-5 500g 3222 A2 103721 Ethyl chlorooxoacetate 4755-77-5 100g 3222 A2 100423 Titanium(IV) chloride solution 7550-45-0 100ml 3222 A2 103877 Acetic Anhydride 108-24-7 1L 3222 A3 103874 Polyphosphoric acid 8017-16-1 1kg 3222 A3 103695 Chlorosulfonic acid 7790-94-5 100g 3222 A3 103694 Chlorosulfonic acid 7790-94-5 100g 3222 A3 103880 Methanesulfonic acid 75-75-2 500ml 3222 A3 103883 Oxalyl chloride 79-37-8 100ml 3222 A3 103889 Thiodiglycolic acid 123-93-3 500g 3222 A3 103888 Tetrafluoroboric acid 50% 16872-11-0 1L 3222 A3 103886 Tetrafluoroboric acid 50% 16872-11-0 1L 3222 A3 102969 sulfuric acid 7664-93-9 500 mL 2428 A7 102970 hydrochloric acid (37%) 7647-01-0 500 mL 2428 A7 102971 hydrochloric acid (37%) 7647-01-0 500 mL 2428 A7 102973 formic acid (88%) 64-18-6 500 mL 2428 A7 102974 hydrofloric acid (49%) 7664-39-3 500 mL 2428 A7 103320 Ammonium Hydroxide conc.
    [Show full text]
  • Heterocyclic Compounds with Biological Meaning
    Heterocyclic compounds with biological meaning 1 Heterocyclic compounds Cyclic, organic compounds which besides carbon atoms have one or more heteroatom (other elements than C). Heterocyclic atoms: – nitrogen, N – sulphur, S – oxygen, O – phosphorus, P – barium, Ba – zinc, Zn – silicon, Si. 2 Heterocyclic compounds From the biological point of view, the most important are heterocyclic compounds with 5- and 6-membered rings, containing: S, N, O. Most of the heterocyclic compounds have their common names. Substituent’s position in the ring is described by : – number – position of heteroatom – no. 1 – Greek letter – describes carbon atom the closest to heteroatom as a, then β and γ, respectively. 3 Heterocyclic compounds Heterocyclic compounds are: • widespread in nature • biologically active • some of them are toxic (e.g. coniine, coumarin and derivatives). Occurrence in: • natural dyes - heme, chlorophyll • alkaloids – atropine and nicotine • amino acids such as tryptophan and histidine • enzymes, nucleoproteins, antibiotics • vitamins • many synthetic pharmaceuticals. 4 Heterocyclic compounds Aromatic character of heteroatom-containing ring comes from aromatic sextet which consists of: • „not bound” electron pairs of heteroatoms • four electrons π from carbon atoms Pyrrole Furane Thiophen 5 5- membered ring heterocyclic compounds with one heteroatom 5-membered rings: • contain mostly oxygen, sulphur and nitrogen • are flat • are aromatic 6 5- membered ring heterocyclic compounds with two heteroatoms oxazole imidazole thiazole pyrazole 7 5- membered ring heterocyclic compounds With one heteroatom With two heteroatoms Condensation products with benzene 8 Pyrrole and derivatives • Pyrrole derivatives: • pyrroline • pyrrolidone • proline, • Hydroksyproline. • Condensation’s products of pyrrole with benzene: – indole, – tryptophan, – serotonin. • Condensation’s products of pyrrole with formaldehyde: – heme – hemoglobin – billirubin – porphyrins – Biliverdin.
    [Show full text]
  • Heterocyclic Compounds
    Gábor Krajsovszky Heterocyclic compounds ISBN: 978-615-5722-01-1 © Gábor Krajsovszky Responsible editor: Gábor Krajsovszky Publisher’s reader: István Mándity Translated by Péter Tétényi Department of Organic Chemistry Pharmaceutical Faculty Semmelweis University Budapest, 2018 Acknowledgements The editor wants to express many thanks to Dr. István Mándity, who is Associate Professor and Director of Department of Organic Chemistry, for the careful proofreading service of the current manuscript, as well as to Dr. Péter Tétényi, who is Assistant Professor, for the translation to English language. Moreover, the editor renders many thanks to Mrs. Ferenc Juhász and Ms. Nikoletta Zlatzky laboratory assistants for drawing material of the figures. Dr. Gábor Krajsovszky Associate Professor Department of Organic Chemistry Literature used Alan R. Katritzky, Charles W. Rees: Comprehensive Heterocyclic Chemistry Parts 2-3, 4-6, 7 Pergamon Press 1984 Oxford • New York • Toronto • Sydney • Paris • Frankfurt T. Eicher, S. Hauptmann, A. Speicher: The Chemistry of Heterocycles Structure, Reactions, Syntheses, and Applications Wiley-VCH GmbH 2003 Weinheim E. Breitmaier, G. Jung: Organische Chemie Grundlagen, Stoffklassen, Reaktionen, Konzepte, Molekülstruktur Georg Thieme Verlag 1978, 2005 Stuttgart • New York Clauder Ottó: Szerves kémia II/2. Egyetemi jegyzet Semmelweis OTE Budapest, 1980 Bruckner Győző: Szerves kémia III−1. Tankönyvkiadó, Budapest, 1964 Természettudományi Lexikon − Harmadik kötet Clauder Ottó: 'Heterociklusos vegyületek' címszó, 155-161.
    [Show full text]
  • Catalytic Asymmetric Di Hydroxylation
    Chem. Rev. 1994, 94, 2483-2547 2483 Catalytic Asymmetric Dihydroxylation Hartmuth C. Kolb,t Michael S. VanNieuwenhze,* and K. Barry Sharpless* Department of Chemistry, The Scripps Research Institute, 10666 North Torfey Pines Road, La Jolla, California 92037 Received Ju/y 28, 1994 (Revised Manuscript Received September 14, 1994) Contents 3.1.4. Differentiation of the Hydroxyl Groups by 2524 Selective, Intramolecular Trapping 1. Introduction and General Principles 2483 3.1.5. Miscellaneous Transformations 2525 2. Enantioselective Preparation of Chiral 1,2-Diols 2489 3.2. Preparation of Chiral Building Blocks 2527 from Olefins 3.2.1. Electrophilic Building Blocks 2527 2.1. Preparation of Ligands, Choice of Ligand, 2489 Scope, and Limitations 3.2.2. Chiral Diol and Polyol Building Blocks 2529 2.1.1. Preparation of the Ligands 2490 3.2.3. Chiral Monohydroxy Compounds Derived 2529 from Diols 2.1 -2. Ligand Choice and Enantioselectivity Data 2490 3.2.4. 5- and 6-Membered Heterocycles 2530 2.1.3. Limitations 2491 3.3. Preparation of Chiral Auxiliaries for Other 2530 2.2. Reaction Conditions 2493 Asymmetric Transformations 2.2.1. Asymmetric Dihydroxylation of the 2493 3.3.1. Preparation of 2530 “Standard Substrates” (1 R,2S)-trans-2-phenylcyclohexanol 2.2.2. Asymmetric Dihydroxylation of 2496 3.3.2. Optically Pure Hydrobenzoin (Stilbenediol) 2531 Tetrasubstituted Olefins, Including Enol and Derivatives Ethers 4. Recent Applications: A Case Study 2536 2.2.3. Asymmetric Dihydroxylation of 2496 Electron-Deficient Olefins 5. Conclusion 2538 2.2.4. Chemoselectivity in the AD of Olefins 2497 6. References and Footnotes 2542 Containing Sulfur 2.3.
    [Show full text]
  • A Concise Review on Phthlazine Derivatives and Its Biological Activities
    Aswathy. J et al /J. Pharm. Sci. & Res. Vol. 11(7), 2019, 2526-2532 A Concise Review on Phthlazine Derivatives and its Biological Activities Aswathy. J M.Pharm, Department of Pharmaceutical Chemistry, Ezhuthachan College of Pharmaceutical Sciences, Marayamuttom Neyyattinkara, Trivandrum, India-695124 Abstract Phthalazine has good attention in the field of research study due to its wide spectrum of biological activity and therapeutic applications. Phthalazine is a good lead compound for the synthesis of novel drugs. There is a growing interest in the synthesis of several phthalazines derivatives as better drug candidates for the treatment of various diseases. Phthalazine contains a strong pharmacophoric moiety and ring structure it attracts the researchers to this nucleus for the synthesis of novel drugs. Through this review, introduce a new way for a researcher by introducing this nucleus and develop a novel class of drugs who have a better therapeutic profile. In this review, mainly discuss the different pharmacological activity of phthalazine which has already discussed by the researcher. These reports have resulted in a great number of contributions in diverse areas of interest. This study may produce a new way for the researchers to design and develop the phthalazine derivatives with good pharmacological activities. Keywords: Anticancer drug, anticonvulsant activity, antimicrobial agent, phthalazine and tuberculosis. INTRODUCTION activities of phthalazine (figure 1) and phthalazin-1(2H)- Phthalazine is a nitrogen-containing heterocyclic one (figure 2), encouraged us for the designing of new compound. Several research studies are focused on the molecules [1]. phthalazine nucleus due to their wide applicability. Phthalazine derivatives are promising drug candidate for PHARMACOLOGICAL ACTIVITIES OF PHTHALAZINE the treatment of various diseases.
    [Show full text]
  • Tetrazinebox: a Structurally Transformative Toolbox Qing-Hui Guo, Jiawang Zhou, Haochuan Mao, Yunyan Qiu, Minh T
    pubs.acs.org/JACS Article TetrazineBox: A Structurally Transformative Toolbox Qing-Hui Guo, Jiawang Zhou, Haochuan Mao, Yunyan Qiu, Minh T. Nguyen, Yuanning Feng, Jiaqi Liang, Dengke Shen, Penghao Li, Zhichang Liu, Michael R. Wasielewski, and J. Fraser Stoddart* Cite This: J. Am. Chem. Soc. 2020, 142, 5419−5428 Read Online ACCESS Metrics & More Article Recommendations *sı Supporting Information ABSTRACT: Synthetic macrocycles capable of undergoing allosteric regulation by responding to versatile external stimuli are the subject of increasing attention in supramolecular science. Herein, we report a structurally transformative tetracationic cyclophane containing two 3,6-bis(4-pyridyl)-l,2,4,5-tetrazine (4-bptz) units, which are linked together by two p-xylylene bridges. The cyclophane, which possesses modular redox states and structural post-modifications, can undergo two reversibly consecutive two-electron reductions, affording first its bisradical dicationic counterpart, and then subsequently the fully reduced species. Furthermore, one single-parent cyclophane can afford effectively three other new analogs through box- to-box cascade transformations, taking advantage of either reductions or an inverse electron-demand Diels−Alder (IEDDA) reaction. While all four new tetracationic cyclophanes adopt rigid and symmetric box-like conformations, their geometries in relation to size, shape, electronic properties, and binding affinities toward polycyclic aromatic hydrocarbons can be readily regulated. This structurally transformative tetracationic cyclophane performs a variety of new tasks as a result of structural post-modifications, thus serving as a toolbox for probing the radical properties and generating rapidly a range of structurally diverse cyclophanes by efficient divergent syntheses. This research lays a solid foundation for the introduction of the structurally transformative tetracationic cyclophane into the realm of mechanically interlocked molecules and will provide a toolbox to construct and operate intelligent molecular machines.
    [Show full text]
  • Non-Empirical Calculations on the Electronic Structure of Olefins and Aromatics
    NON-EMPIRICAL CALCULATIONS ON THE ELECTRONIC STRUCTURE OF OLEFINS AND AROMATICS by Robert H. Findlay, B.Sc. Thesis presented for the Degree of Doctor of philosophy University of Edinburgh December 1973 U N /),, cb CIV 3 ACKNOWLEDGEMENTS I Wish to express my gratitude to Dr. M.H. Palmer for his advice and encouragement during this period of study. I should also like to thank Professor J.I.G. Cadogan and Professor N. Campbell for the provision of facilities, and the Carnegie Institute for the Universities of Scotland for a Research Scholarship. SUMMARY Non-empirical, self-consistent field, molecular orbital calculations, with the atomic orbitals represented by linear combinations of Gaussian-type functions have been carried out on the ground state electronic structures of some nitrogen-, oxygen-, sulphur- and phosphorus-containing heterocycles. Some olefins and olefin derivatives have also been studied. Calculated values of properties have been compared with the appropriate experimental quantities, and in most cases the agreement is good, with linear relationships being established; these are found to have very small standard deviations. Extensions to molecules for which there is no experimental data have been made. In many cases it has been iôtrnd possible to relate the molecular orbitals to the simplest member of a series, or to the hydrocarbon analogue. Predictions of the preferred geometry of selected molecules have been made; these have been used to predict inversion barriers and reaction mechanisms. / / The extent of d-orbital participation in molecules containing second row atoms has been investigated and found to be of trivial importance except in molecules containing high valence states of the second row atoms.
    [Show full text]
  • Recent Developments in Chemistry of Phthalazines
    stry: Cu i rre em n t El-Azm et al., Organic Chem Curr Res 2015, 4:1 h R C e c s i e n a DOI: 10.4172/2161-0401.1000132 a r Organic Chemistry c g r h O ISSN: 2161-0401 Current Research ResearchReview Article Article OpenOpen Access Access Recent Developments in Chemistry of Phthalazines Fatma SM Abu El-Azm*, Mahmoud R Mahmoud, and Mohamed H Hekal Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt Abstract This review highlights the methods used for the synthesis of phthalazine derivatives and fused phthalazinones. Their reactivity and synthetic importance were investigated. Phthalazine derivatives can be used as building blocks for heterocycles as well as fused heterocyclic compounds. Keywords: Phthalazine derivatives; Pyrazolophthalazines; were tested [59]. An expeditious one-pot method has been developed Indazolophthalazines; [1,2,4] Triazolophthalazines for the synthesis of aryl, heteryl thiadiazinyl-phthalazin-1,4-diones via a multicomponent approach. Reaction of phenacyl bromides 22 with Introduction thiocarbohydrazide 23 and phthalic anhydride afforded corresponding Among a large variety of nitrogen-containing heterocyclic aryl thiadiazinyl-phthalazine-1,4-diones 24 similarly, reaction of compounds, heterocyclic containing hydrazine has received 3-(2-bromoacetyl) coumarins 25 with thiocarbohydrazide and phthalic considerable attention because of their pharmacological properties anhydride afforded required heterylthiadiazinyl-phthalazine-1,4- and clinical applications [1-6]. Phthalazine derivatives were reported diones 26 under the same reaction conditions in excellent yields [60] to possess anticonvulsant [7-10], cardiotonic [11], antitumor [12-16], (Scheme 6). antihypertensive [17-19], antithrombotic [20], a ntidiabetic [21,22], Hydrazines with 2-acyl benzoic acids: Kirill et al.
    [Show full text]
  • Download-PDF
    Journal of Pharmaceutical Research International 27(6): 1-15, 2019; Article no.JPRI.44928 ISSN: 2456-9119 (Past name: British Journal of Pharmaceutical Research, Past ISSN: 2231-2919, NLM ID: 101631759) An Overview of Different Synthetic Routes for the Synthesis of Phthalazine Derivatives Smita Singh1,2 and Nitin Kumar3* 1IFTM University, Muradabad, Uttar Pradesh, India. 2K. N. Modi Institute of Pharmaceutical Education and Research, Modinagar, Uttar Pradesh, India. 3Department of Pharmacy, Sushant School of Health Sciences, Ansal University, Gurugram, 122003, India. Authors’ contributions This work was carried out in collaboration between both authors. Both authors read and approved the final manuscript. Article Information DOI: 10.9734/JPRI/2019/v27i630189 Editor(s): (1) Dr. Carlos M. Contreras, Unidad Periferica Xalapa, Instituto de Investigaciones Biomedicas, UNAM, Mexico and Instituto de Neuroetologia, Universidad Veracruzana, Mexico. (2) Dr. Jinyong Peng, Professor, College of Pharmacy, Dalian Medical University, Dalian, China. (3) Dr. Ali Nokhodchi, Professor of Pharmaceutics and Drug Delivery, School of Life Sciences, University of Sussex, UK. Reviewers: (1) Sangeetha A/P Arullappan, Jalan Universiti, Malaysia. (2) Manojit Pal, University of Hyderabad, India. (3) B. Satish Jadhav, Balbhim College, India. Complete Peer review History: http://www.sdiarticle3.com/review-history/44928 Received 14 October 2018 Review Article Accepted 31 December 2018 Published 08 June 2019 ABSTRACT This review paper describes the different synthetic routes used for the synthesis of substituted phthalazine derivatives. Phthalazines have been used as building blocks for the synthesis of a new molecule with heterocyclic structure. These new molecules are highly useful in medicinal chemistry for the researchers leading to the further development of new molecules which have potency and effectiveness to produce a desired pharmacological response.
    [Show full text]
  • Design, Synthesis, Characterization and Biological Evaluation of Some Novel Cinnolo Piperazine Derivatives
    Innovare International Journal of Pharmacy and Pharmaceutical Sciences ISSN- 0975-1491 Vol 6, Issue 5, 2014 Academic Sciences Original Article DESIGN, SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SOME NOVEL CINNOLO PIPERAZINE DERIVATIVES SHRUTI VARSHNEY*, DR.VIKAS SAXENA Rakshpal Bahadur College of pharmacy Bareilly, Uttar Pradesh, India. Email: [email protected] Received: 12 Mar 2014 Revised and Accepted: 02 Apr 2014 ABSTRACT Objective: To design and synthesize a series of substituted 4-(p-amino piperazine) cinnoline-3- carboxamide derivatives and evaluate for anti- microbial activity. Method: A novel series of substituted 4-(p-amino piperazine) cinnoline-3- carboxamide (4a-g) derivatives were synthesized by reacting substituted 4-amino cinnoline 3-carboxamide (3a-g) with DMF and o-chloro piperazine. Substituted 4-amino cinnoline 3-carboxamide (3a-g) were synthesized by reaction of substituted phenyl hydrazono cyano acetamide (2a-g) with anhydrous AlCl 3 and chlorobenzene in nitrogenous environment. Substituted phenyl hydrazono (cyano) acetamide was synthesized by reaction of substituted aniline diazonium chloride (1a-g) with CH 3COONa and ethanol. Substituted aniline diazonium chloride were synthesized by substituted aniline with conc HCl. and sodium nitrite .The synthesized compounds were characterized by IR, NMR and Mass spectral data. The synthesized compounds were screened for their antibacterial and antifungal activity against 4 pathogenic bacteria and 2 pathogenic funguses. Results : The compound 4a , 4c and 4g shows potent antimicrobial activity in comparison to standard drugs while other compounds showed moderate activity. Further all the compounds are obtained in good purity. Conclusion : All the compounds synthesized were checked for their purity and spectral analysis shows their structural confirmation.
    [Show full text]
  • Heterocyclic Chemistry at a Glance Other Titles Available in the Chemistry at a Glance Series
    Heterocyclic Chemistry at a Glance Other Titles Available in the Chemistry at a Glance series: Steroid Chemistry at a Glance Daniel Lednicer ISBN: 978-0-470-66084-3 Chemical Thermodynamics at a Glance H. Donald Brooke Jenkins ISBN: 978-1-4051-3997-7 Environmental Chemistry at a Glance Ian Pulford, Hugh Flowers ISBN: 978-1-4051-3532-0 Natural Product Chemistry at a Glance Stephen P. Stanforth ISBN: 978-1-4051-4562-6 The Periodic Table at a Glance Mike Beckett, Andy Platt ISBN: 978-1-4051-3299-2 Chemical Calculations at a Glance Paul Yates ISBN: 978-1-4051-1871-2 Organic Chemistry at a Glance Laurence M. Harwood, John E. McKendrick, Roger Whitehead ISBN: 978-0-86542-782-2 Stereochemistry at a Glance Jason Eames, Josephine M Peach ISBN: 978-0-632-05375-9 Reaction Mechanisms at a Glance: A Stepwise Approach to Problem-Solving in Organic Chemistry Mark G. Moloney ISBN: 978-0-632-05002-4 Heterocyclic Chemistry at a Glance Second Edition JOHN A. JOULE The School of Chemistry, The University of Manchester, UK KEITH MILLS Independent Consultant, UK This edition fi rst published 2013 © 2013 John Wiley & Sons, Ltd Registered offi ce John Wiley & Sons Ltd, The Atrium, Southern Gate, Chichester, West Sussex, PO19 8SQ, United Kingdom For details of our global editorial offi ces, for customer services and for information about how to apply for permission to reuse the copyright material in this book please see our website at www.wiley.com. The right of the author to be identifi ed as the author of this work has been asserted in accordance with the Copyright, Designs and Patents Act 1988.
    [Show full text]
  • Synthesis and Biological Evaluation of Isatin Incorporated Quinoxalines As Anti-Tubercular Agents
    Int. J. Pharm. Sci. Rev. Res., 47(2), November - December 2017; Article No. 13, Pages: 67-70 ISSN 0976 – 044X Research Article Synthesis and Biological Evaluation of Isatin incorporated Quinoxalines as Anti-Tubercular Agents 1* 1 1 1 1 2 U. Usha Rani , P. Sivappa Naidu , G. Sukanya , P. Sri Datha , S. Pramod Kumar , Venkata Rao Vutla* 1 Department of Pharmaceutical Chemistry, Riper, Ananthapur, AP, India. 2 Department of Pharmaceutical Chemistry, Chebrolu Hanumaiah Institute of Pharmaceutical Sciences, Guntur, AP, India. *Corresponding author’s E-mail: [email protected] Received: 07-11-2017; Revised: 28-11-2017; Accepted: 13-12-2017. ABSTRACT Heterocyclic compounds are very much used as therapeutic agents. Indole, an important class of nitrogen, containing heterocyclic with wide variety of biological activities. Isatin is a derivative of indole which is indole-2, 3 Dione. Isatin is reported for anti- tubercular activity. Quinoxaline is also reported for various biological activities. So, a scheme was designed and isatin incorporated quinoxaline were prepared to improve biological activity. In the present research isatin incorporated quinoxaline (1, 1A, 1B and 1C) were prepared, and were characterized by using TLC, IR, NMR and MASS spectral data. They were evaluated for anti-tubercular activity. Among those derivatives, compound 1 showed good activity. Keywords: Isatin, tubercular activity, Quinoxaline. INTRODUCTION Isatis tinctoria and Calanthe discolor. It has also been found as a component of the secretion from the parotid eterocyclic compounds play a major role in gland of Bufo frogs, and in humans as it is a metabolic medicinal chemistry and synthesis of drugs. derivative of adrenaline Isatin belongs to the class of Modification of the structure of heterocyclic H organic compounds known as Indolines.
    [Show full text]