Amidines: Their Synthesis, Reactivity, and Applications in Heterocycle Synthesis
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Synthesis of 1,2,4 Oxadiazol-5-Imine, 1,2,4-Triazol-3-Imine and Derivatives: a Substituted Cyanamide-Based Strategy for Heterocycle Synthesis
Synthesis of 1,2,4 oxadiazol-5-imine, 1,2,4-triazol-3-imine and derivatives: A Substituted Cyanamide-based Strategy for Heterocycle Synthesis Shreesha V. Bhat A thesis submitted in partial fulfilment of the requirements of the University of Lincoln for the degree of Doctor of Philosophy June 2017 Statement of Originality “I, Shreesha V. Bhat, hereby declare that this submission is my own work and to the best of my knowledge it contains no materials previously published or written by another person, or substantial proportions of material which have been published or accepted for the award of any other degree or diploma at University of Lincoln or any other educational institution, except where references have been made in the thesis. Any contribution made to the research by others, with whom I have worked at the University of Lincoln or elsewhere, is explicitly acknowledged in the thesis. I also declare that the intellectual content of this thesis is the product of my own work, except to the extent that assistance from others in the project's design and conception or in style, presentation and linguistic expression is acknowledged.” (Shreesha V. Bhat) ii | P a g e Abstract Considering the importance of nitrogen-rich heterocycles in drug discovery, a novel strategy towards heterocycle synthesis was envisioned using cyanamide chemistry. Synthesis which involve mild conditions, avoids multi-step sequence and non-toxic reagents are desirable for generation of large combinatorial libraries of drug molecules. We envisaged that the NCN linkage of the cyanamide as well as the concomitant use of the nucleo-and electrophilic centres of the cyanamide could provide a novel synthetic route towards nitrogen heterocycles. -
Part One Amino Acids As Building Blocks
Part One Amino Acids as Building Blocks Amino Acids, Peptides and Proteins in Organic Chemistry. Vol.3 – Building Blocks, Catalysis and Coupling Chemistry. Edited by Andrew B. Hughes Copyright Ó 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 978-3-527-32102-5 j3 1 Amino Acid Biosynthesis Emily J. Parker and Andrew J. Pratt 1.1 Introduction The ribosomal synthesis of proteins utilizes a family of 20 a-amino acids that are universally coded by the translation machinery; in addition, two further a-amino acids, selenocysteine and pyrrolysine, are now believed to be incorporated into proteins via ribosomal synthesis in some organisms. More than 300 other amino acid residues have been identified in proteins, but most are of restricted distribution and produced via post-translational modification of the ubiquitous protein amino acids [1]. The ribosomally encoded a-amino acids described here ultimately derive from a-keto acids by a process corresponding to reductive amination. The most important biosynthetic distinction relates to whether appropriate carbon skeletons are pre-existing in basic metabolism or whether they have to be synthesized de novo and this division underpins the structure of this chapter. There are a small number of a-keto acids ubiquitously found in core metabolism, notably pyruvate (and a related 3-phosphoglycerate derivative from glycolysis), together with two components of the tricarboxylic acid cycle (TCA), oxaloacetate and a-ketoglutarate (a-KG). These building blocks ultimately provide the carbon skeletons for unbranched a-amino acids of three, four, and five carbons, respectively. a-Amino acids with shorter (glycine) or longer (lysine and pyrrolysine) straight chains are made by alternative pathways depending on the available raw materials. -
Durham E-Theses
Durham E-Theses Meisenheimer complexes: some structural, equilibrium and kinetic studies Khan, Hassan Akhtar How to cite: Khan, Hassan Akhtar (1973) Meisenheimer complexes: some structural, equilibrium and kinetic studies, Durham theses, Durham University. Available at Durham E-Theses Online: http://etheses.dur.ac.uk/8740/ Use policy The full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that: • a full bibliographic reference is made to the original source • a link is made to the metadata record in Durham E-Theses • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders. Please consult the full Durham E-Theses policy for further details. Academic Support Oce, Durham University, University Oce, Old Elvet, Durham DH1 3HP e-mail: [email protected] Tel: +44 0191 334 6107 http://etheses.dur.ac.uk MEISENHEIMER COMPLEXES: SOME STRUCTURAL, EQUILIBRIUM AND KINETIC STUDIES by HASSAN AKHTAR KHAN M.Sc. (Pakistan) A thesis submitted for the degree of Doctor of Philosophy in the University of Durham. JUNE 1973 Chemistry Department 1 6 JUL 1973 SEOriON ACKNOWLEDGEMENTS It is with gratitude that I thank my supervisor, Dr. M.R. Crampton, for his inspiration, generous help and encouragement throughput the course of this work. I would also like to thank the many staff members and technical staff of the department for their co-operation. -
Mild Reductive Functionalization of Amides Into N‐Sulfonylformamidines
http://www.diva-portal.org This is the published version of a paper published in ChemistryOpen. Citation for the original published paper (version of record): Trillo, P., Slagbrand, T., Tinnis, F., Adolfsson, H. (2017) Mild Reductive Functionalization of Amides into N-Sulfonylformamidines. ChemistryOpen, 6(4): 484-487 https://doi.org/10.1002/open.201700087 Access to the published version may require subscription. N.B. When citing this work, cite the original published paper. Permanent link to this version: http://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-138585 DOI:10.1002/open.201700087 Mild Reductive Functionalization of Amides into N- Sulfonylformamidines Paz Trillo,[a] Tove Slagbrand,[a] Fredrik Tinnis,*[a] and Hans Adolfsson*[a, b] The development of aprotocolfor the reductivefunctionaliza- tion of amides into N-sulfonylformamidines is reported. The one-pot procedure is based on amild catalytic reduction of tertiaryamides into the corresponding enamines by the use of Mo(CO)6 (molybdenum hexacarbonyl) and TMDS (1,1,3,3-tetra- methyldisiloxane). The formed enamines were allowed to react with sulfonyl azidestogive the target compounds in moderate to good yields. The amidine functional group is frequently found in biological- ly activecompounds possessing anti-inflammatory,antibacteri- al, antiviral, antibiotic, and anestheticproperties.[1] They are also employed as intermediates and precursors in organic syn- thesis of importantheterocyclic compounds such as imida- zoles, quinazolines,isoquinolines, and pyrimidines.[2] Further- more, amidines are employed as ligandsinmetal complexes and as protecting groups for primary amines.[3] Scheme1.Preparation of amidines through a–c) electrophilic amide activa- The stability of amides makes this functional group valuable tion and d) reductive functionalization of amides. -
A Publication of Reliable Methods for the Preparation of Organic Compounds
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. -
EICG-Hot Spots: EICG Appendix C
INFORMAL REVIEW DRAFT [Note: The pre-existing regulation text is set forth below in normal type. The original proposed amendments are shown in underline to indicate additions and strikeout to indicate deletions. Additional proposed modifications are shown in double-underline to indicate additions and double-strikeout to indicate deletions. The square brackets “[ ]” are used to indicate minor adjustments to text (e.g., page numbers and adoption dates) that will be updated upon adoption of the proposed amendments.] APPENDIX C FACILITY GUIDELINE INDEX (FACILITY "LOOK-UP" TABLE) INFORMAL REVIEW DRAFT This Page Intentionally Left Blank INFORMAL REVIEW DRAFT APPENDIX C - I RESPONSIBILITIES OF ALL FACILITIES INFORMAL REVIEW DRAFT NOTES FOR APPENDIX CFACILITY GUIDELINE INDEX APPENDIX C-I RESPONSIBILITIES OF ALL FACILITIES NOTHING IN THIS APPENDIX SHALL BE CONSTRUED AS REQUIRING THAT SOURCE TESTING BE CONDUCTED FOR SUBSTANCES SET FORTH IN THIS APPENDIX. FURTHER, IN CASES WHERE A SUBSTANCE SET FORTH HEREIN IS NOT PRESENT AT A PARTICULAR FACILITY, THE FACILITY OPERATOR SHALL NOT ATTEMPT TO QUANTIFY THE EMISSIONS OF SUCH SUBSTANCE, BUT SHALL PROVIDE ADEQUATE DOCUMENTATION TO DEMONSTRATE TO THE DISTRICT THAT THE POSSIBLE PRESENCE OF THE SUBSTANCE AT THE FACILITY HAS BEEN ADDRESSED AND THAT THERE ARE NO EMISSIONS OF THE SUBSTANCE FOR SPECIFIED REASONS. Substances emitted by a particular device or process may not be limited to those listed in this Facility Guideline Index. THIS APPENDIX IS NOT AN EXHAUSTIVE LIST. ALL FACILITIES ARE RESPONSIBLE FOR IDENTIFYING AND ACCOUNTING FOR ANY LISTED SUBSTANCE USED, MANUFACTURED, FORMULATED, OR RELEASED. This Facility Guideline Index is arranged in alphabetical order. The first part of the index, Appendix C-I, lists devices common to many industries and the second part of the index, Appendix C-II, lists industry types. -
Information to Users
INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. University Microfilms International A Bell & Howell Information C om pany 300 North Z eeb Road. Ann Arbor. Ml 48106-1346 USA 313/761-4700 800 521-0600 Order Number 9120692 Part 1. Synthesis of fiuorinated catecholamine derivatives as potential adrenergic stimulants and thromboxane A 2 antagonists. Part 2. -
SODIUM METHOXIDE, 30% in Methanol
AKS761.5 - SODIUM METHOXIDE, 30% in methanol SODIUM METHOXIDE, 30% in methanol Safety Data Sheet AKS761.5 Date of issue: 10/26/2016 Version: 1.0 SECTION 1: Identification 1.1. Product identifier Product name : SODIUM METHOXIDE, 30% in methanol Product code : AKS761.5 Product form : Mixture Physical state : Liquid Formula : CH3NaO Synonyms : SODIUM METHYLATE METHANOL, SODIUM SALT Chemical family : METAL ALCOHOLATE 1.2. Recommended use of the chemical and restrictions on use Recommended use : Chemical intermediate For research and industrial use only 1.3. Details of the supplier of the safety data sheet GELEST, INC. 11 East Steel Road Morrisville, PA 19067 USA T 215-547-1015 - F 215-547-2484 - (M-F): 8:00 AM - 5:30 PM EST [email protected] - www.gelest.com 1.4. Emergency telephone number Emergency number : CHEMTREC: 1-800-424-9300 (USA); +1 703-527-3887 (International) SECTION 2: Hazard(s) identification 2.1. Classification of the substance or mixture GHS-US classification Flammable liquids Category 3 H226 Acute toxicity (oral) Category 3 H301 Acute toxicity (dermal) Category 3 H311 Acute toxicity (inhalation:vapor) Category 3 H331 Skin corrosion/irritation Category 1B H314 Serious eye damage/eye irritation Category 1 H318 Specific target organ toxicity (single exposure) Category 1 H370 Specific target organ toxicity (single exposure) Category 3 H336 Full text of H statements : see section 16 2.2. Label elements GHS-US labeling Hazard pictograms (GHS-US) : GHS02 GHS05 GHS06 GHS07 GHS08 Signal word (GHS-US) : Danger Hazard statements (GHS-US) : H226 - Flammable liquid and vapor H301+H311+H331 - Toxic if swallowed, in contact with skin or if inhaled H314 - Causes severe skin burns and eye damage H318 - Causes serious eye damage H336 - May cause drowsiness or dizziness H370 - Causes damage to organs Precautionary statements (GHS-US) : P280 - Wear protective gloves/protective clothing/eye protection/face protection P307 + P311 - If exposed: Call a poison center/doctor P210 - Keep away from heat, open flames, sparks. -
Alkoxylated Fatty Esters and Derivatives from Natural
(19) TZZ ¥¥ZZ_T (11) EP 2 633 008 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 211/00 (2006.01) 20.03.2019 Bulletin 2019/12 (86) International application number: (21) Application number: 11838497.3 PCT/US2011/057595 (22) Date of filing: 25.10.2011 (87) International publication number: WO 2012/061092 (10.05.2012 Gazette 2012/19) (54) ALKOXYLATED FATTY ESTERS AND DERIVATIVES FROM NATURAL OIL METATHESIS ALKOXYLIERTE FETTESTER UND DERIVATE AUS EINER ERDÖLMETATHESE ESTERS GRAS ALCOXYLÉS ET DÉRIVÉS À PARTIR DE LA MÉTATHÈSE D’HUILES NATURELLES (84) Designated Contracting States: • HOLLAND, Brian AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Deerfield GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO IL 60015 (US) PL PT RO RS SE SI SK SM TR • MALEC, Andrew, D. Chicago (30) Priority: 25.10.2010 US 406556 P IL 60657 (US) 25.10.2010 US 406570 P • MASTERS, Ronald, A. 25.10.2010 US 406547 P Glenview IL 60025 (US) (43) Date of publication of application: • MURPHY, Dennis, S. 04.09.2013 Bulletin 2013/36 Libertyville IL 60048 (US) (73) Proprietor: Stepan Company •SKELTON,Patti Northfield, Illinois 60093 (US) Winder GA 30680 (US) (72) Inventors: • SOOK, Brian • ALLEN, Dave, R. Lawrenceville Chicago GA 30045 (US) IL 60610 (US) • WIESTER, Michael •ALONSO,Marcos Chicago Chicago IL 60625 (US) IL 60645-4922 (US) • WOLFE, Patrick, Shane • BERNHARDT, Randal, J. Palatine Antioch IL 60074 (US) IL 60002 (US) • BROWN, Aaron (74) Representative: Müller, Christian Stefan Gerd Chicago ZSP Patentanwälte -
United States Patent Office Patented Jan
3,017,356 United States Patent Office Patented Jan. 16, 1962 1. 2 rated aliphatic radical, a cycloaliphatic radical, an aryl 3,017,356 radical, an aralkyl radical, an alkaryl radical, an alkoxy WillianPROCESS B. Hughes, OF andINHIBITING Verner L. Stronberg,CORROSION Webster alkyl radical, an aryloxyalkyl radical, and the like; and Groves, Mo., assignor's to Petroite Corporation, Wii A is an alkylene group; for example, ethylene and propyl mington, Del, a corporation of Delaware ene radicals, such as No Drawing. Original application Mar. 3, 1958, Ser. No. 718,391 Divided and this application Nov. 23, 1959, Ser. No. 854,553 -CH2CH2CH 15 Claims. (C. 252-8.55) CH-CH2 O B This application is a division of Serial No. 718,391, CHs filed March 3, 1958. This invention relates to esters of cyclic amidines of -CH-CH-CH,- the formula gh, CHis O 15 -bH-bH In general, the amidine esters are prepared by reacts o-o-c- ing a hydroxyaliphatic cyclic amidine ()-ROH with less where (A) and (B) are cyclic amidine-containing radicals, than a stoichiometric amount of a polycarboxylic acid to for example, imidazoline and tetrahydropyrimidine radi form a half ester cals (hereafter referred to as “amidine esters'). More 20 particularly, this invention relates to esters wherein. A contains one type of cyclic amidine ring and B contains (a)-R-O C-Z-COH the same or another type not selected in A. This inven which is subsequently reacted with an amidine forming tion also relates to a process of preparing these com polyamine to form the amidine ester pounds which comprises reacting a hydroxy-containing 25 O cyclic amidine with less than a stoichiometric amount of a polycarboxylic acid to form a partial ester and then re Q-R-O-)-2- acting this partial ester with a polyamine capable of form More specifically, the corrosion inhibiting aspect of this ing a second amidine ring of the same or different type. -
Acroseal Packaging Your Solution for Air- and Moisture- Sensitive Reagents
AcroSeal Packaging Your solution for air- and moisture- sensitive reagents Extra dry solvents Deuterated solvents Organometallic compounds Reagents in solution Organics Introduction Since the launch of AcroSealTM packaging we have introduced a new septum, which helps preserve product quality for longer. In addition, our AcroSeal portfolio has been expanded to include a broad range of solvents, organometallics, reagents in solution and organic compounds. In this brochure we have categorized our products under chemical families to make it easier to locate the product you need. Introduction Page no. AcroSeal packaging highlights 3 AcroSeal packaging performance 4 New 25mL AcroSeal packaging 4 Solvents Extra dry solvents 5-7 Solvents for biochemistry 7 Deuterated solvents 7 Organometallics Grignard reagents 8-10 Organoaluminiums 11 Organolithiums 11 Organosodiums 12 Organotins 12 Organozincs 12 Reagents in solution Amines 13 Boranes 13 Halides 14-15 Hydrides 15 Oxides 16 Silanes 16 Other reagents in solution 17 Organics Aldehydes 18 Amines 18 Epoxides 18 Halides 19 Phosphines 19 Silanes 19 Other organics 20 How to use AcroSeal packaging 21 Alphabetical index 22-23 2 Introduction AcroSeal packaging: drier reagents for longer When using air- and moisture-sensitive solvents and reagents, it is essential that these products are not only as dry as possible when you first use them, but they should remain dry in storage as well. Through the innovative quadrant-style screw cap and specially designed septum, AcroSeal packaging ensures that you have access to high-quality and low-moisture products every use, guaranteeing improved yield and consistency of your research experiments while reducing chemical waste. AcroSeal packaging highlights New septum developed from a polymeric elastomer with an inert fluoropolymer-coated surface, preserves product quality for longer with better re-seal around needle punctures. -
Poly(Vinylammonium Formate) and Process for Making Amidine
Europaisches Patentamt (19) European Patent Office Office europeenpeen des brevets EP0617 054B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) intci.e: C08F 8/12, C08F 8/44 of the grant of the patent: 04.12.1996 Bulletin 1996/49 (21) Application number: 94104538.7 (22) Date of filing: 22.03.1994 (54) Poly(vinylammonium formate) and process for making amidine-containing polymers Poly(Vinylammoniumformiat) und Verfahren zur Herstellung von Amidinegruppen enthaltender Polymeren Poly(formiate vinylique d'ammonium) et procede de preparation de polymeres contenant de groupes amidine (84) Designated Contracting States: (72) Inventor: Ford, Michael Edward BE DE FR GB NL Coopersburg, PA 18036 (US) (30) Priority: 25.03.1993 US 36757 (74) Representative: Kador & Partner Corneliusstrasse 15 (43) Date of publication of application: 80469 Miinchen (DE) 28.09.1994 Bulletin 1994/39 (56) References cited: (73) Proprietor: AIR PRODUCTS AND CHEMICALS, EP-A- 0 374 646 EP-A- 0 528 409 INC. DE-A-3 715 824 US-A- 4 393 174 Allentown, PA 18195-1501 (US) US-A- 4 943 676 DO ^> o Is- CO Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice the Patent Office of the Notice of shall be filed in o to European opposition to European patent granted. opposition a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. a. 99(1) European Patent Convention). LU Printed by Jouve, 75001 PARIS (FR) EP 0 617 054 B1 Description FIELD OF THE INVENTION 5 This invention relates to poly(vinylammonium formate) and to a process for its manufacture.