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Tetrahydrocyclopenta[ e ]pyrido[3,2‐ b ][1,4]diazepine and ‐cyclopenta[ e ]pyrido[2,3‐ b ][1,4]diazepine derivatives
Author(s) -
Savelli Francesco,
Boido Alessandro,
Vazzana Iana,
Sparatore Fabio
Publication year - 1987
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.5570240641
Subject(s) - diazepine , chemistry , derivative (finance) , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , financial economics , economics
In pursuing the study on compounds obtained by condensation of N ‐monoalkylated aromatic and hetero‐aromatic diamines with α‐ and β‐ketoesters, 7,8,9,10‐tetrahydrocyclopenta[ e ]pyrido[3,2‐ b ][1,4]diazepin‐6(5 H )‐ones 4a, 4b and 5,7,8,10‐tetrahydrocyclopenta[ e ]pyrido[2,3,‐ b ][l,4]diazepin‐9 H )‐ones 5a, 5b were prepared starting from 2,3‐diaminopyridine or 2,3‐diamino‐5‐chloropyridine and ethyl 2‐oxo‐cyclopentanecarboxylate. Compounds 4a,b and 5a,b suffer thermally induced ring contraction to the imidazolone derivatives 8a,b and 7a,b respectively and are unsuitable for preparing diazepinone derivatives. Thus the methylated diazepinones 15, 17 and 18 , stable on heating, were prepared. Compound 17 was transformed into the clozapine analogue 22 , through the diazepinthione 20 and its S ‐methyl derivative 21 .