Synthesis of trisubstituted 1,3-oxazin-6-ones via base-catalyzed ring-opening annulation of cyclopropenones with N-(pivaloyloxy)amides

被引：10

作者：

Matsuda, Takanori ^{[1
]}

Yamanaka, Kentaro ^{[1
]}

Tabata, Yuki ^{[1
]}

Shiomi, Takahiro ^{[1
]}

机构：

[1] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, 1-3 Kagurazaka, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 15期

关键词：

Cyclopropenone; Ring opening; Annulation; Amide; Oxazinone; C-H ACTIVATION; N-METHOXYBENZAMIDES; CYCLOADDITION REACTIONS; REACTION PATHWAY; BENZAMIDES; BOND; DIPHENYLCYCLOPROPENONE; CARBONYLATION; HETEROCYCLES; SUBSTITUTION;

D O I：

10.1016/j.tetlet.2018.02.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-catalyzed [3+3]-type annulation between cyclopropenones and N-(pivaloyloxy)amides is reported. The formal insertion of a 1,3-N,O-dipole into a cyclopropenone C-C bond yields a six-membered azalactone structure. In the presence of catalytic K2CO3 at 60 degrees C in THF, the disubstituted cyclopropenone couples with benzamides, acrylamides, and a phenylacetamide to produce 2,4,5-trisubstituted 1,3-oxazin-6-ones in 23-99% yield. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：1458 / 1460

页数：3

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