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
收藏
页码：229 / 244
页数：16
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