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Novel synthesis of 5,11‐dihydro‐6 H ‐pyrido[2,3‐ b ]‐[1,4]benzodiazepin‐6‐ones and related studies
Author(s) -
Oklobdžija M.,
Comisso G.,
Decorte E.,
Fajdiga T.,
Gratton G.,
Moimas F.,
Toso R.,
Šunjić V.
Publication year - 1983
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.5570200535
Subject(s) - chemistry , ring (chemistry) , congener , stereochemistry , transformation (genetics) , combinatorial chemistry , organic chemistry , biochemistry , gene
5,11‐Dihydro‐6 H ‐pyrido[2,3‐6][1,4]benzodiazepin‐6‐one (1), a basic intermediate in the preparation of 11‐α‐aminoacetyl derivatives with important biological activities, has been obtained by a three‐step synthesis starting from easily available isatoic anhydride and anhydro ornithine. Some model cyclisation reactions leading to 5‐member ring derivatives 10 and 12 instead of 7‐member ring analogues of 1 , are reported. Easy transformations of the tetrahydro congener of 1 , i.e., compound 4 into 19 , which actually represents a tetrahedral intermediate in the transformation of 5 into 4 , is noticed. Further rearrangement of 19 into spiro compound 20 , and return of the latter into 5 is described.