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Quinazolines et benzodiazépines‐1, 4. LVI. Oxadiazolo‐1, 2, 4[4, 5‐d] benzodiazépines‐1, 4: synthése et passage aux oxazolo [3, 2‐d] benzodiazépines‐1, 4
Author(s) -
Jaunin R.,
Oberhänsli W. E.,
Hellerbach J.
Publication year - 1972
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.19720550831
Subject(s) - chemistry , yield (engineering) , nitrile , tricyclic , stereochemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
Abstract The tricyclic derivatives 4–14 can be prepared by 1, 3‐dipolarcycloaddition of the appropriate nitrile oxides on the corresponding 1, 4‐benzodiazepines. NaBH 4 reduction of the esters 12–14 was found to proceed very readily; starting from 13 it is possible, by proper reaction conditions, to get in good yield either the monoalcohol 19 or the aminodiol 20 . The alcohols 19 and 23 undergo an acid‐catalysed rearrangement which produces the amidoximes 24 and 26 . The determination of the structure of 24 by X‐ray diffraction analysis is also presented.