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Attempts at new synthesis of 5,11 ‐Dihydro‐6 H ‐pyrido[2,3‐b][1,4]benzodiazepin‐6‐one
Author(s) -
Oklobdžija M.,
Comisso G.,
Decorte E.,
Kovač T.,
Angeli C.,
Moimas F.,
Za P.,
Zonno 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.5570200536
Subject(s) - chemistry , intramolecular force , ring (chemistry) , condensation , derivative (finance) , medicinal chemistry , condensation reaction , stereochemistry , computational chemistry , organic chemistry , catalysis , thermodynamics , physics , financial economics , economics
Attempting some new approaches to 5,11‐dihyro‐6 H ‐pyrido[2,3‐ b ][1,4]benzodiazepin‐6‐one ( 6 ), compounds 8, 10 and 11 were prepared. Ring enlargement of 4 into 6 failed, as well as condensation of 10 and 11 into ID, which is the potential precursor of pirenzepin (11‐[2′‐(4″‐methylpiperazin‐1″‐yl)]acetyl derivative of 6 ) via an envisaged intramolecular Diels‐Alder reaction. Model compounds 5 and 13 were prepared and their behaviour in analogous reactions explained the failures of the intended transformations of 4 , as well as of condensation of 10 and 11 .