Reaction of β‐aminocrotonamide with dibasic acid derivatives | Zendy

Sato Masayuki | Zendy; Ogasawara Hiromichi | Zendy; Kato Tetsuzo | Zendy

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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 .

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