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Reaction of β‐aminocrotonamide with dibasic acid derivatives
Author(s) -
Sato Masayuki,
Ogasawara Hiromichi,
Kato Tetsuzo
Publication year - 1983
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.5570200120
Subject(s) - chemistry , dibasic acid , sodium methoxide , derivative (finance) , yield (engineering) , adipate , succinic anhydride , pyridine , organic chemistry , phthalic anhydride , medicinal chemistry , polymer chemistry , methanol , materials science , financial economics , economics , metallurgy , catalysis
Reaction of β‐aminocrotonamide ( 1 ) with succinic anhydride gave β‐succinaminocrotonamide ( 3a ), which was treated with base to cyclize to 3,4‐dihydro‐6‐methyl‐4‐oxo‐2‐pyrimidinepropanoic acid ( 4a ). Similarly, pyrimidinepentanoic acid derivative 4b was prepared from compound 1 and glutaric anhydride. Reaction of compound 1 with glutarate, adipate, and phthalate gave the corresponding pyrimidines 4b, 4c and 4d , while reaction of compound 1 with malonate gave 2‐hydroxypyridine derivative 11 and dimethylpyrimidinone 4e . Reaction of dimethyl fumarate with compound 1 in the presence of methoxide gave a poor yield of pyrrolo[3,4‐ c ]pyridine derivative 13 .