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Synthesis of 5‐Amino‐9‐benzyl‐6‐formyl‐4‐methoxy‐2‐pivaloylamino‐7,8‐dihydropyrimido[4,5‐ b ]azepine. A potentially useful intermediate towards the synthesis of pyrimidoazepine based folic acid derivatives
Author(s) -
Miller Michael L.,
Ray Partha S.
Publication year - 1996
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.5570330208
Subject(s) - chemistry , azepine , pyrimidine , nitrile , cycloaddition , ring (chemistry) , intramolecular force , alkyne , aldehyde , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Synthesis of the title compound is described via an intramolecular 1,3‐dipolar cycloaddition reaction between the pyrimidine nitrile oxide 24 and an alkyne dipolarophile tethered to the 6‐position of the pyrimidine ring. The resulting isoxazolopyrimidoazepine cycloadduct 25 was treated with molybdenum hexacarbonyl to provide the titled enamino aldehyde 26 .