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Synthesis and Reactions of Novel Thienotetrahydroisoquinoline Compounds

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Synthesis and Reactions of Novel Thienotetrahydroisoquinoline Compounds Synthesis and reactions of novel thienotetrahydroisoquinoline compounds Remon M. Zaki*, Adel M. Kamal El-Dean, Shaban M. Radwan Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt Síntesis y reacciones de nuevos compuestos de tienotetrahidroisoquinolina Síntesi i reaccions de nous derivats de tientetrahidroisoquinolina Recibido:2 de octubre de 2011; aceptado: 16 de febrero de 2012 RESUMEN for synthesis of triazepinopyrimido 10. Reaction of 1 with carbon disulfide in pyridine afforded the pyrimidinethione La cloroacetilación de 1-Aminocarboxamida 1 propor- 13 which underwent double Mannich reaction to give the cionó la cloroacetilamina 2 la cual experimentó el cierre novel thiadiazinopyrimido compound 14. Reaction of tet- del anillo al ser sometida a reflujo con anhídrido acético rahydroisoquinoline thione 15 with 2-chloromethylbenz- para proporcionar el derivado clorometilpirimido 3. Este imidazole followed by Thorpe-Zeigler cyclization to afford último compuesto experimenta reacciones de sustitución the aminobenzoimidazolyl 18 which proved its versatil- nucleofílica con varias aminas primarias y secundarias ity as starting material for synthesis of novel heterocyclic que, a través de la reacción de Mannich proporcionaron compounds 19-22. las imidazopirimidotienoisoquinolinas 5a-c. El compuesto 1 reacciona con anhídrido ftálico en ácido acético y DMF Keywords: Imidazole, Triazepine, Thiadiazine, Pyrimidine, para proporcionar phthalimido- e isoindolopymimidotieno- synthesis, reactions tetrahidroisoquinolinas 6, 7 respectivamente. La reacción con dietilmalonato proporcionó el pirimidocar- boxylato 8 que reacciona con hidrato de hidrazina para dar RESUM la carbohidrazida 9, la cual reacciona con trietilorthofor- mato en la síntesis de triazepinopirimido 10. La reacción La cloracetilació de la 1-Aminocarboxamida 1 proporcio- de 1 con sulfuro de carbono en piridina proporcionó la piri- na la cloroacetilamina 2 la qual experimenta el tancament midintiona 13 que después de doble reacción de Mannich de l‘anell al ser sotmesa a reflux amb anhídrid acètic per proporciona el nuevo derivado tiadiazinopirimido 14. La proporcionar el derivat clorometilpirimido 3. Aquest últim reacción de la tetrahidroisoquinolintiona 15 con 2-chloro- derivat experimenta reaccions de substitució nucleofílica metilbenzimidazole y posterior ciclación de Thorpe-Zeigler amb varies amines primàries i secundàries que, mitjançant proporcionó el aminobenzoimidazolilo 18 que demostró su la reacció de Mannich proporcionen les imidazopirimi- versatilidad como material de partida para la síntesis de dotienoisoquinolines 5a-c. El producte 1 reacciona amb los nuevos derivados heterocíclicos 19-22. anhídrid ftàlic en àcid acètic i DMF per proporcionar fta- limido- i isoindolopimimido-tien-tetrahidroisoquinolines 6, Palabras clave: Imidazol, Triazepina, Tiadiazina, Pirimidi- 7 respectivament. na, síntesis, reacciones La reacció amb dietilmalonat proporcionà el pirimidocar- boxylat 8 que reacciona amb hidrat de hidrazina per donar la carbohidrazida 9, la qual reacciona amb trietilortofor- SUMMARY mat en la síntesi de triazepinopirimido 10. La reacció d’1 amb sulfur de carboni en piridina proporciona la pirimidin- Chloroacetylation of 1-Aminocarboxamide 1 afforded the tiona 13 que després de doble reacció de Mannich propor- chloroacetylamino 2 which underwent ring closure upon ciona el nou derivat tiadiazinopirimido 14. La reacció de la reflux with acetic anhydride to afford the chloromethyl- tetrahidroisoquinolintiona 15 amb 2-clorometilbenzimida- pyrimido 3. The latter compounds underwent nucleophilic zol i subseqüent ciclació de Thorpe-Zeigler proporciona substitution reactions with various primary and second- el aminobenzoimidazolil derivat 18 cosa que demostrà la ary amines which underwent Mannich reaction to give the seva versatilitat com material de partida per a la síntesi imidazopyrimidothienoisoquinolines 5a-c. Compound 1 dels nous derivats heterocíclics 19-22. react with phthalic anhydride in acetic acid and DMF to afford phthalimido and isoindolopyrimido thienotetrahy- Paraules clau: Imidazol, Triazepina, Tiadiazina, Pirimidina, droisoquinoline 6, 7 respectively. síntesi, reaccions Reaction with diethylmalonate afforded the pyrimidocar- boxylate 8 which react with hydrazine hydrate to give the carbohydrazide 9 which react with triethyl orthoformate *Corresponding author: [email protected] 424 AFINIDAD LXVIII, 556, Noviembre - Diciembre 2012 INTRODUCTION hydroisoquinolines and incorporating many heterocyclic rings fused to this moiety which were proved to have sig- The tetrahydroisoquinoline family of alkaloids includes nificant antibacterial and antifungal activities 23-26. potent cytotoxic agents that display a range of biological properties such as antitumor, antimicrobial, anti-inflamma- tory and anti-leukemic activities 1,2. RESULTS AND DISCUSSION: Tetrahydropyrimidothienoisoquinolines and tetrahydro- pyrimidothienoquinolines are useful compounds as anti- Reaction of aminocarboxamide 1 with chloro acetylchlo- anaphylactics, anti-inflammatories, and bacteriophage in- ride in dioxan followed by treating with sodium carbon- hibitors 3. Thienoquinolines are reported to exhibit a broad ate solution afforded the chloroacetylamino derivative 2, spectrum of biological effects. Some of them are useful as which underwent ring closure using acetic anhydride to memory enhancers 4, antiallergics 5, anti-inflammatories, afford the chloromethyl compound 3. The latter can be ob- immuno regulators, analgesics and antipyritics 6. Others tained by heating compound 1 with excess chloro acetyl- are known to possess a good antibacterial 7 and antiana- chloride on water bath followed by treatment with sodium phylactic activities 8. carbonate solution. The structure of the produced com- Also, Thienopyrimidines have long been the subject of pound 3 was elucidated on the basis of 1H NMR spectra chemical and biological research. The interest in these which revealed the disappearance of signals at d 6.80 ppm compounds is related to their broad range of biological ac- characteristic for NH2 group and appearance of signals at tivity, which is displayed by representatives of all the pos- d 4.60 ppm characteristic for CH2 and at 10.70 ppm for sible structural combinations of the thiophene and pyrimi- NH and confirmed by mass spectrum (m/z) 390.19 (M+) dine systems. Some thienopyrimidines display analgesic 9, which in agreement with the postulated structure. Chlo- antipyretic 10,11, anti-inflammatory 12-15, and anti-allergenic roacetyl derivative 3 underwent nucleophilic substitution effects 16-18. These compounds have been studied as anti- reactions with various primary and secondary amines in neoplastic agents 19 and for lowering the cholesterol level refluxed ethanol to afford 10-arylaminomethyl derivatives in the cardiovascular system 20,21. 4a-f. Treatment of compounds 4 a-c with formaldehyde These findings have led us to continue our work on thi- under Mannish conditions afforded imidazopyrimido de- enopyrimidine derivatives 22. In continuation of our work, rivatives 5 a-c (Scheme 1). we reported new methods for preparation of thienotetra- SCHEME 1 Synthesis of the imidazopyrimidothienotetrahydroisoquinoline derivatives Cl NH O NH2 NH NH2 2 O Cl S O Cl N S O N N N 1 Dioxan 2 O O O Cl Cl Fusion Ac2O R2 Cl N N N R R NH R1 NH 1 2 NH N N N N EtOH S O S O O O 3 4 a-f a: R1=Ph, R2=H b: R1=p-MePh, R2=H HCHO/dioxan c: R1=p-OMePh, R2=H stirring d: R1=R2=Et e: R , R = -O(CH ) 1 2 2 4 N N R f: R1, R2= -(CH2)5 N N N O S O 5 a-c AFINIDAD LXVIII, 556, Noviembre - Diciembre 2012 425 When compound 1 was allowed to react with phthalic an- Compound 8 reacts with hydrazine hydrate to give the cor- hydride in boiling acetic acid. The reaction stopped at the responding carbohydrazide derivative 9 which was used stage of formation of 3-phthalimido derivative 6, whereas as versatile starting material for the synthesis of other in boiling DMF a deeper condensation occurs to give a de- heterocyclic compounds. Thus, reaction of 9 with triethyl rivative of a new heterocyclic system namely 5-morpholin- orthoformate in presence of acetic acid yielded the triaz- 4-yl-1,2,3,4-tetrahydro-14-oxoisoindolo [1’’,2’’:2’,3’]pyrim- epino derivative 10. While the reaction with acetyl acetone ido[4’,5’:4,5]thieno[2,3-c]isoquinolin-8-one (7). Reaction of in ethanol gives dimethylpyrazolo derivative 11. Conden- compound 1 with diethyl malonate in acetic acid afforded sation of compound 9 with aromatic aldehydes gives the Schiff’s base followed by elimination of ethanol to give corresponding Schiff’s base 12 (Scheme 3). the S-ethoxycarbonylmethyl derivative 8 (Scheme 2). SCHEME 2 Reaction of aminocarboxamide with phthalic anhydride and diethyl malonate O O N N O N NH N N 2 N O S N O O S 7 O 6 Phthalic anhydride/ AcOH Phthalic anhydride/ DMF NH2 NH2 N N O S 1 O CH2(CO2Et)2 AcOH O N O NH N N O S 8 O SCHEME 3 Codensation reactions of tetrahydropyrimidothienoisoquinolinecarbohydrazide O N NH N N N N O S 10 O HC(OEt)3 EtOH H NH2NH2.H2O N NH2 8 N O EtOH NH N N O S 9 O PhCHO EtOH/piperidine Ac2CH2/ EtOH H Ph N N N N O N NH N N N O O S NH 12 O N N O S 11 O 426 AFINIDAD LXVIII, 556, Noviembre - Diciembre 2012 SCHEME 4 Synthesis of tetrahydrothiadiazinopyrimidothienoisoquinoline H S CS2/pyridine N NH2 NH NH N 2 N N N S O S O O 13 O 1 HCHO/ PhNH2 S N N N N N O S O 14 SCHEME 5 Mechanism of double Mannish reaction H H C=N C O + NH 2 H 2 H S SH N N + H C=N NH NH 2 N N O N O S N S O O S N Ph + N H S NH N N : NH O O N S NH O N Ph O N S O H C O H S N Ph N S .. -H2O N Ph NH N N O N O NH CH S H H N 2 O + O + N S O S + N -H S + Ph N N N N CH O NH 2 N S N O O N S O Reaction of compound 1 with carbondisulfide in pyridine The mechanism of double Mannish reaction to afford com- by heating on water bath for 10 hours afforded the py- pound 14 was suggested in the following scheme.
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