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Facile synthesis of 6‐aryl‐5 H ‐8‐oxa‐4 b , 7‐diaza‐benzo[ a ]azulen‐9‐one derivatives, new tricyclic heterocycles
Author(s) -
Praveen Cherukupally,
Rao Javvaji Rama,
Reddy Padi Pratap,
Mukkanti Kaga,
Reddy Gade Srinivas
Publication year - 2008
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.5570450421
Subject(s) - chemistry , tricyclic , indole test , phenacyl , aryl , hydroxylamine , hydrolysis , hydroxylamine hydrochloride , stereochemistry , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl
8‐Oxa‐ 4b ,7‐diaza‐benzo[ a ]azulene‐9‐one system, a new tricyclic heterocyclic framework is designed through a simple and convenient synthetic sequence. Its 6‐aryl derivatives are synthesized starting from ethyl indole‐2‐carboxylate. Reaction of differently substituted phenacyl bromides with ethyl indole‐2‐carboxylate, treatment of the resultant N‐substituted indole‐2‐carboxylates with hydroxylamine hydrochloride to provide corresponding oximes, subsequent ester hydrolysis followed by dehydrative cyclisation furnished the desired compounds 5 a‐g .