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Polycondensed heterocycles. I. Synthesis of 11‐oxo‐5 H , 11 H ‐pyrrolo[2,1‐ c ][1,4]benzothiazepine, Derivative of a novel ring system
Author(s) -
Nacci V.,
Garofalo A.,
Fiorini I.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220204
Subject(s) - pyrrole , chemistry , ring (chemistry) , hydrolysis , ethyl chloroformate , derivative (finance) , amide , intramolecular force , medicinal chemistry , organic chemistry , stereochemistry , financial economics , economics
The synthesis of the title compound 4 by cyclization of 1‐(2‐ethoxycarbonylthiobenzyl)pyrrole 9 , prepared by treating with ethyl chloroformate the 1‐(2‐mercaptobenzyl)pyrrole 7 previously obtained by debenzylation of 1‐(2‐benzylthiobenzyl)pyrrrole 6 , failed. On the other hand 4 was successfully synthesized by intramolecular cyclization of 1‐(2‐mercaptobenzyl)pyrrole‐2‐carboxylic acid 15 by DMAP ‐catalyzed DCC method. The pyrrole 6 and 1‐(2‐benzylthiobenzyl)pyrrole‐2‐carboxaldehyde 11 were useful as starting materials to obtain 1‐(2‐benzylthiobenzyl)pyrrole‐2‐carbonitrile 13 , which was hydrolyzed to corresponding amide 16 . Debenzylation of 16 afforded 1‐(2‐mercaptobenzyl)pyrrole‐2‐carboxyamide 17 , whose hydrolysis led to required acid 15 .