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Synthesis of novel 1‐substituted [1,3]thiazolo[3,2‐ a ]‐[1,5]benzodiazepine derivatives from 1,5‐benzodiazepine‐2‐thiones and α‐halogen carbonyl compounds
Author(s) -
Janciene Regina,
Stumbreviciute Zita,
Podeniene Daiva,
Puodziunaite Benedikta D.,
Black Steve,
Husbands Stephen M.
Publication year - 2006
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.5570430424
Subject(s) - chemistry , ring (chemistry) , enamine , benzodiazepine , halogen , salt (chemistry) , acetal , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , molecule , organic chemistry , catalysis , biochemistry , alkyl , receptor
AbstractA number of substituted 4H,5H,6H‐thiazolo[3,2‐ a ][1,5]benzodiazepinium salts 2a‐h, 5, 9 , which are based on the novel thiazolobenzodiazepine system, were prepared by condensation‐cyclization of 1,5‐benzodiazepine‐2‐thiones 1a‐f, h, 4 with α‐haloketones, as well as with α‐bromoacetaldehyde diethyl acetal. The structure and stereochemistry of the ring system obtained were investigated by 1 H and 13 C nmr spectroscopy: the additional heterocyclic nucleus was found to appreciably influence the conformational mobility of the heptatomic ring. Upon treatment of salt 2d with alkali the presence of the base enamine structure in solution has been postulated.