A NEW APPROACH TO IMIDAZO[1,2-a]PYRIDINE DERIVATIVES AND THEIR APPLICATION TO THE SYNTHSES OF NOVEL 2H-PYRANO[2′,3′:4,5] IMIDAZO[1,2-a]PYRIDIN-2-ONE DERIVATIVES

被引：4

作者：

Abe, Takashi ^{[1
]}

Okumura, Yukihisa ^{[1
]}

Suga, Hiroyuki ^{[1
]}

Kakehi, Akikazu ^{[1
]}

机构：

[1] Shinshu Univ, Fac Engn, Dept Chem & Mat Engn, Nagano 3808553, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 01期

关键词：

Cyclization; Synthesis; 3-Methylene-2(3H)-imidazo[1,2-a]pyridinone; 3-Vinylimidazo[1,2-a]pyridin-2-ol; Pyrano[2 ',3 ':4,5]imidazo[1,2-a]pyridine; NITROGEN-BRIDGED HETEROCYCLES; SYNTHETIC METHOD;

D O I：

10.3987/COM-09-S(S)41

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-[Bis(methylthio)methylene]-2(3H)-imidazo[1,2-a]pyridinones were prepared from the S-alkylation of pyridinium 1-[1-carbamoyl-1-[(methylthio) thiocarbonyl]]methylides with methyl iodide followed by the alkaline treatment of the resulting pyridinium salts. The reactions of these 3-methylene-2(3H)-imidazo[1,2-a]pyridinones with some ethyl cyano- or acyl-substituted acetates in the presence of a base did not afford the initially expected 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives, but, instead of them, provided ethyl 3[2-hydroxyimidazo[1,2-a]pyridin-3-yl]acrylates. The thermolyses of these acrylates without any solvent under reduced pressure gave the corresponding 2H-pyrano[2',3':4,5]imidazo[1,2-a]pyridine-2-one derivatives.

引用

页码：439 / 454

页数：16

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