Utility of α-oxoketene and α-cyanoketene thioacetals in heterocyclic syntheses: Synthesis of some new benzothiazepine derivatives

Synthetic Communications

Volumn 41, Issue 3, 2011, Pages 331-340

  Mohamed, Mounir A A ^a  

^a Sohag University   (Egypt)

Author keywords

oxoketene dithioacetals; Active methylene; benzothiazepines; piperidine

Indexed keywords

1 [2 [(2 AMINOETHYL)IMINO] 4 METHYL 2,3 DIHYDRO 1,5 BENZOTHIAZEPIN 3 YL]ETHANONE; 1 [4 METHYL 2 (METHYLTHIO)BENZO[B][1,5]THIAZEPIN 3 YL]ETHANONE; 1,11 DIMETHYL 3 OXO 3H PYRANO[4,3 B][1,5]BENZOTHIAZEPINE 4 CARBONITRILE; 2 (METHYLTHIO) 4 OXO 4,5 DIHYDROBENZO[B][1,5]THIAZEPINE 3 CARBONITRILE; 3 AMINO 2 PHENYL 2H PYRAZOLO[3,4 B][1,5]BENZOTHIAZEPIN 4(5H) ONE; 3 AMINO 2H PYRAZOLO[3,4 B][1,5]BENZOTHIAZEPIN 4(5H) ONE; 3 AMINOISOXAZOLO[3,4 B][1,5] BENZOTHIAZEPIN 4(5H) ONE; 3 IMINO 1,11 DIMETHYL 3H PYRANO[4,3 B][1,5]BENZOTHIAZEPINE 4 CARBONITRILE; 3 METHYL 1,11 DIOXO 1,2,10,11 TETRAHYDRO PYRIDO[4,3 B][1,5]BENZOTHIAZEPINE 4 CARBOXYLATE; 3,4 DIMETHYL 2 PHENYL 2H PYRAZOLO[3,4 B][1,5]BENZOTHIAZEPINE; 3,4 DIMETHYL 2H PYRAZOLO[3,4 B][1,5]BENZOTHIAZEPINE; 3,4 DIMETHYLISOXAZOLO[3,4 B][1,5]BENZOTHIAZEPINE; 4 ACETYL 1 IMINO 3 METHYL 1H PYRANO[4,3 B][1,5]BENZOTHIAZEPIN 11(10H) ONE; 4 ACETYL 3 METHYLPYRIDO[4,3 B][1,5]BENZOTHIAZEPINE 1,11(2H,10H) DIONE; 5,6 DIMETHYL 2,3 DIHYDRO 1H [1,4]DIAZEPINO[5,6 B][1,5]BENZOTHIAZEPINE; BENZOTHIAZEPINE DERIVATIVE; ETHYL 1 IMINO 3 METHYL 11 OXO 10,11 DIHYDRO 1H PYRANO[4,3 B][1,5] BENZOTHIAZEPINE 4 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS;

EID: 78751500850     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903538644     Document Type: Article

References (26)

1. (a) Mane, R. A.; Ingle, D. B. Synthesis and biological activity of some new 1,5-benzothia-zepines containing thiazole moiety. Ind. J. Chem., Sect. B 1982, 21B, 973;
2. (b) Attia, A.; Abdel-salam, O. I.; Abo-Ghalia, M. H.; Amr, A. E. Chemical and biological reactivity of newly synthesized 2-chloro-6-ethoxy-4- acetylpyridines. Egypt. J. Chem. 1995, 38, 543-553.
3. 0-yl)resorcinols as potential antifeedants. Ind. J. Chem., Sect. B 1993, 32, 404-406.
4. Satyanarayana, K.; Rao, M. N. A. Synthesis of 3-[4-[2,3-dihydro-2- (substitutedaryl)-1,5-benzothiazepin-4-yl]phenyl]sydnones as potential anti-inflammarory agents. Ind. J. Pharm. Sci. 1993, 55, 230-234.
5. DeSarro, G.; Chimirri, A.; DeSarro, A.; Gitto, R.; Grasso, S.; Zappala, M. 5H-[1,2,4]-Oxadiazolo[5,4-d]benzothiazepines as anticonvulsant agents in DBA=2 mice. Eur. J. Med. Chem. 1995, 30(12), 925-929. (Pubitemid 26004610)
6. Gronowitz, S. The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives; Wiley: New York, 1991; vol. 44.
7. (a) Pinto, I. L.; Jarvest, R. L.; Serafinowska, H. T. The synthesis of 5-alkoxy and 5-amino substituted thiophenes. Tetrahedron Lett. 2000, 41(10), 1597-1600;
8. (b) Luker, T. J.; Beaton, H. G.; Whiting, M.; Mete, A.; Cheshire, D. R. Palladium-catalysed amination of electron-deficient halothiophenes. Tetrahedron Lett. 2000, 41(40), 7731-7735.
9. (a) Bohlmann, F.; Zdero, C.; Gronowitz, S. Thiophene and Its Derivatives; John Wiley & Sons: New York, 1985; part 1, p. 261;
10. (b) Koike, K.; Jia, Z.; Nikaido, T.; Liu, Y.; Zhao, Y.; Guo, D. Echinothiophene, a novel benzothiophene glycoside from the roots of Echinops grijissii. Org. Lett. 1999, 1(2), 197-198.
11. (a) Kiess, H. Conjugated Conducting Polymers; Springer: New York, 1992; vol. 102;
12. (b) Roncali, J. Conjugated poly(thiophenes): Synthesis, functionalization, and applications. Chem. Rev. 1992, 92(4), 711-738;
13. (c) Schopf, G.; Kossmehl, G. Polythiophenes- Electrically conductive polymers. Adv. Polym. Sci. 1997, 129, 1.
14. Watanabe, M.; Yamamoto, T.; Nishiyama, M. Synthesis of novel (bis) (diarylamino)-thiophenes via palladium-catalysed reaction of (di)bromothiophenes. Chem. Commun. 2000, 133-135.
15. Katritzky, A. R.; Odens, H. H.; Zhang, S. Novel synthesis of 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones and 2H-1,4-benzothiazin-3(4H)-ones. J. Org. Chem. 2001, 66, 6792.
16. Prakash, O.; Kumar, A.; Sadana, A.; Prakash, R.; Singh, S. P.; Claramunt, R. M.; Sanz, D.; Alkorta, I.; Elguero, J. Study of the synthesis of chalcone analogs of dehydroacetic acid and o-aminothiophenol: Synthesis and structure of 1,5-benzothiazepines and 1,4-benzothiazines. Tetrahedron 2005, 61, 6642-4451.
17. Braun, R. U.; Muller, T. J. One-pot synthesis of dihydrobenzo[b][1,4] thiazepines and dia-zepines via coupling isomerisation-cyclocondensation sequences. Tetrahedron 2004, 60(42), 9463-9469.
18. Levai, A. Oxazepines and thiazepines, 41: Synthesis of 4-aryl-2,3-dihydro-2-styryl-1,5-benzothiazepines by the reaction of (E,E)-cinnamylidene-acetophenones with 2-aminothiophenol and their conversion into 2,2-disubstituted 3-acetyl-2,3-dihydrobe-zothiazoles. J. Heterocycl. Chem. 2004, 41, 399403.
19. Karthikeyan, S. V.; Peruma, S. A facile tandem protocol for the synthesis of the regioselective synthesis of novel thienobenzothiazepines. Tetrahedron Lett. 2007, 48(13), 2261-2265.
20. 0-benzoxazole) derivatives. Synthesis 1994, 152.
21. Farhat, M. F.; El-Saghier, A. M. M.; Makhlouf, M. A.; Kreddan, K. M.; Elmezoughi, A. B. Ketene-N,S-acetals in heterocyclic synthesis, part 1: Synthesis of N-phenyl-2-ylidene and 2,5-diylidene thiazolidinone derivatives. J. Sulfur Chem. 2007, 28(6), 563-572.
22. El-Saraf, G. A.; El-Sayed, A. M.; El-Saghier, A. M. M. One-pot PTC synthesis of poly-fused pyrazoles. Heteroatom 2003, 14(3), 211-217.
23. Abdel-Ghany, H. A.; El-Saghier, A. M. M.; El-Sayed, A. M. A novel synthesis of hetero-cyclic compounds from a-oxoketene-S,S-acetal. Synth. Commun. 1996, 26(22), 4289-4297.
24. El-Saghier, A. M. M.; Maihub, A. A.; Al-Shirayda, H. A. A novel synthesis of imida-zo[2,1-d][1,2,4]triazine and imidazo[2,1-d][1,2,5]triazepine derivatives via ketene-N,S-acetal. Synth. Commun. 1996, 27(14), 2433-2444.
25. El-Sayed, A. M.; Abdel-Ghany, H. A.; El-Saghier, A. M. M. A novel synthesis of pyra-no(2,3-c)-, 1,3-oxazino(2,3-b)-, 1,2,4-triazolo(3,4-b)-, oxazolo(2,3-b)-, furano(2,3-c), and 3-substituted-(1,5)-benzodiazepin-2-ones. Synth. Commun. 1999, 29(20), 3561-3572.
26. El-Saghier, A. M. M.; Farhat, M. F.; Farhat, M. F. 1,4-Diazepines bearing thieno(2,3-b)thiophene and cyclohexene carboxylate moieties. Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181(7), 1569-1582.