Stereoselective annelation of 3-substituted imidazo[4,5-b]pyridines with cyanoacetylenic alcohols and domino rearrangement of the adducts

被引：6

作者：

Trofimov, Boris A. ^{[1
]}

Andriyankova, Ludmila V. ^{[1
]}

Nikitina, Lina P. ^{[1
]}

Belyaeva, Kseniya V. ^{[1
]}

Mal'kina, Anastasiya G. ^{[1
]}

Dyachenko, Oleg A. ^{[2
]}

Kazheva, Olga N. ^{[2
]}

Chekhlov, Anatolii N. ^{[2
]}

Afonin, Andrei V. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, 1 Favorsky Str, Irkutsk 664033, Russia

[2] Russian Acad Sci, Inst Problems Chem Phys, Chernogolovka 142432, Russia

来源：

ARKIVOC | 2012年

关键词：

Annelation; formamides; imidazopyridines; rearrangement; zwitterions; HIGHLY SELECTIVE INHIBITOR; IMIDAZOPYRIDINE; NITRILES; BYK191023; FACILE; POTENT; SERIES;

D O I：

10.3998/ark.5550190.0013.622

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazo[4,5-b] pyridines are readily annelated (45-50 degrees C, 24-30 h, MeCN) with cyanoacetylenic tertiary alpha-alcohols to give stereoselectively functionalized 1,3-oxazolo[3,2-alpha] imidazo[ 4,5-b] pyridines in 50-88% yields. The adducts undergo a facile stereoselective hydrolytic domino rearrangement to functionalized derivatives of 2,3-diaminopyridines.

引用

页码：229 / 244

页数：16