Triflic Anhydride Mediated Synthesis of Imidazo[1,5-a]azines

被引：75

作者：

Pelletier, Guillaume ^{[1
]}

Charette, Andre B. ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 09期

基金：

加拿大自然科学与工程研究理事会;

关键词：

DIRECT ALKYNYLATION; CYCLIZATION; DERIVATIVES; STRATEGY; REAGENT;

D O I：

10.1021/ol400870b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Imidazo[1,5-a]azines are synthesized in moderate to excellent yields using a mild cyclodehydration/aromatization reaction triggered by the use of triflic anhydride (Tf2O) and 2-methoxypyridine (2-MeOPyr). Various substitution patterns and functional groups were found to be compatible under the optimized conditions. In addition, a 5-bromo-3-aryl derivative was also shown to be active in a Sonogashira cross-coupling and direct arylation reactions. A tertiary amide was compatible as a substrate leading to the synthesis of an imidazo[1,5-a]pyridinium triflate.

引用

页码：2290 / 2293

页数：4

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