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Synthesis of 5 H [l]benzopyrano[3,4‐ b ]pyridin‐5‐one and its derivatives
Author(s) -
Khan Misbahul Ain,
Gemal Andre Luis
Publication year - 1977
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.5570140612
Subject(s) - chemistry , ethyl acetoacetate , methylene , dimethyl acetylenedicarboxylate , ring (chemistry) , medicinal chemistry , stereochemistry , bicyclic molecule , organic chemistry , catalysis , cycloaddition
Abstract 3‐Aminocoumarin undergoes the Skraup reaction to give a new ring system, 5 H [l]benzo‐pyrano[3,4‐b]pyridin‐5‐one (IVa). When 3‐aminocoumarin was condensed with the ethoxy methylene derivatives of active methylene compounds, ethyl acetoacetate, and dimethyl acetylenedicarboxylate, the intermediates Vla‐VIf were formed which on thermal cyclizations afforded other derivatives of 5 H [l ]benzopyrano[3,4‐ b ]pyridin‐5‐one (IVb‐IVf). The nitration of IVa gave IVg.