Tetrahedron p. 3055 - 3058 (1983)
Update date:2022-09-26
Topics:
Narula, Anubhav P. S.
Epstein, Joseph W.
The novel compound, 2-(3-pyridyl)maleimide, 7 was prepared by an efficient sequence involving the synthesis of ethyl 2-(3-pyridyl)acrylate, 3, from ethyl 2-(3-pyridyl)acetate, 1, followed by Michael-addition of HCN (via acetone cyanohydrin-MeOH) to give cyanoester 4.Alteranatively, 4 was prepared from the methyl ester 8 by alkylation with iodoacetonitrile.Acid hydrolysis gave amide-ester 5 which was then cyclized with NaOEt to 2-(3-pyridyl)succimide, 6.Oxidation of 6 to maleimide 7 was achieved with N-chlorosuccinimide in pyridine, to give an overall yield of 58percent.
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