PYRROLE-ANNULATED HETEROCYCLIC-SYSTEMS - SYNTHESIS OF 2H-PYRROLO[3,4-B][1,5]BENZOTHIAZEPINE 4,4-DIOXIDE DERIVATIVES

Authors
DISANTO R COSTI R MASSA S ARTICO M
Citation
R. Disanto et al., PYRROLE-ANNULATED HETEROCYCLIC-SYSTEMS - SYNTHESIS OF 2H-PYRROLO[3,4-B][1,5]BENZOTHIAZEPINE 4,4-DIOXIDE DERIVATIVES, Synthetic communications, 28(13), 1998, pp. 2517-2530
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
28
Issue
13
Year of publication
1998
Pages
2517 - 2530
Database
ISI
SICI code
0039-7911(1998)28:13<2517:PH-SO2>2.0.ZU;2-0
Abstract
Condensation of 2-nitrothiophenol with ethyl propiolate afforded 3-(2- nitrophenylthio)propenoate. Oxidation of sulfur atom to sulfone group gave ethyl 3-(2-nitrophenylsulfonyl)propenoate, which underwent conden sation with tosyl methylisocyanide (TosMIC) to yield ethyl 4-(2-nitrop henylsulfonyl)pyrrole-3-carboxylate. Reduction of nitro group afforded ethyl -(2-aminophenylsulfonyl)-1H-pyrrole-3-carboxylate, which was cy clized to 2H-pyrrolo[3,4-b][1,5] benzothiazepin-10(9H)-one 4,4-dioxide . Similar procedure was used for the synthesis of ro-10-methyl-2H-pyrr olo[3,4-b][1,5]benzothiazepine 4,4-dioxide.