Russian Journal of Organic Chemistry

2-alkoxypropenals as synthetic equivalents of methylglyoxal in the synthesis of heterocycles

NA Keiko, NV Vchislo, LI Larina

Index: Keiko; Vchislo; Larina Russian Journal of Organic Chemistry, 2013 , vol. 49, # 3 p. 428 - 431 Zh. Org. Khim., 2013 , vol. 49, # 3 p. 440 - 443,4

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Citation Number: 5

Abstract

Abstract One-pot synthesis of 2-methylquinoxaline, 3-hydroxy-2-methylimidazo [1, 2-a] pyridine, and 2-methyl-3, 7-dihydroimidazo [1, 2-a] pyrazin-3-one via cycloaddition of N, N- binucleophilic o-phenylenediamine, 2-aminopyridine, and 2-aminopyrazine, respectively, to methylglyoxal generated in situ by hydrolysis of 2-alkoxypropenals is reported for the first time. Thus 2-alkoxypropenals in weakly acidic medium (25–80° C, 1–4 h) are convenient ...