Synthesis of oxazino[4,3-a]indoles by domino addition-cyclization reactions of (1H-indol-2-yl)methanols and vinyl selenones in the presence of 18-crown-6

被引：12

作者：

Palomba, Martina ^{[1
]}

Vinti, Elisa ^{[1
]}

Marini, Francesca ^{[1
]}

Santi, Claudio ^{[1
]}

Bagnoli, Luana ^{[1
]}

机构：

[1] Univ Perugia, Grp Catalysis & Organ Green Chem, Dept Pharmaceut Sci, Via Liceo 1, I-06123 Perugia, Italy

来源：

TETRAHEDRON | 2016年 / 72卷 / 44期

关键词：

Vinyl selenones; Domino reactions; (1H-Indol-2-yl)methanols; Oxazino[4,3-a]indoles; ONE-POT SYNTHESIS; MICHAEL REACTION; N-ALKYLATION; INDOLES; STRATEGY; PYRROLE; ESTERS; ROUTE;

D O I：

10.1016/j.tet.2016.09.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the synthesis of biologically relevant oxazino[4,3-a]indoles by an environmentally friendly Michael addition-cyclization cascade using potassium hydroxide in dichloromethane employing variously substituted vinyl selenones and (1H-indol-2yl)methanols. The addition of 18-crown-6, as a complexing agent, is crucial to achieve high chemo- and regio-selectivity. (C) 2016 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7059 / 7064

页数：6

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