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Quinazolines et benzodiazépines‐1,4. LX Imidazo[5,1‐ c ]benzodiazépines‐1,4
Author(s) -
Jaunin Roland,
Arnold Wolf
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560742
Subject(s) - chemistry , tricyclic , oxalyl chloride , epimer , stereochemistry , nucleophile , yield (engineering) , nuclear magnetic resonance spectroscopy , alkyl , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Abstract Upon treatment with oxalyl chloride followed by reaction with the appropriate nucleophile, the 3‐carbamoyl‐benzodiazepines 6 , 7 and 8 were converted stereospecifically to the tricyclic compounds 12, 13, 14, 16 and 19 . Epimerization of 19 in presence of p ‐toluenesulfonic acid led to 21 . The stereochemistry of these tricyclic compounds and of some of their N(2)‐alkyl derivatives ( 22‐31 ) has been established by NMR. spectroscopy. Under proper reaction conditions, attack by bases on the tricyclic esters 13 and 26 was shown to cause an inversion of the chiral center C(11a) and to yield stereospecifically rearranged products, e.g. 23 from 26 and 33 from 13 .