Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process†,Organic & Biomolecular Chemistry

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Addition of 4-(cyclohex-1-en-1-yl)morpholine on 3-nitroindole: an unprecedented dearomatizing process†
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2016-01-12 00:00:00 , DOI: 10.1039/c5ob02595h
Manuel Andreini _{1,

2,

3,

4,

5} , Fabien Chapellas _{1,

2,

3,

4,

5} , Sonia Diab _{1,

2,

3,

4,

5} , Karine Pasturaud _{1,

2,

3,

4,

5} , Serge R. Piettre _{1,

2,

3,

4,

5} , Julien Legros _{1,

2,

3,

4,

5} , Isabelle Chataigner _{1,

2,

3,

4,

5}

Affiliation

Nucleophilic enamines add spontaneously on heteroarenes 3-nitroindole and benzofuran to form a new C–C bond. With nitroindole 1 and enamine 2a, an unprecedented dearomatizing formal ene reaction occurs in a totally regio- and diastereo-selective manner. With 3-nitrobenzofuran 10 and enamine 2d, the reaction course is different and leads to the generation of a dienylphenol.

中文翻译：

在3-硝基吲哚上添加4-（环己-1-烯-1-基）吗啉：前所未有的脱芳香化过程†

亲核烯胺自发地加在杂芳烃3-硝基吲哚和苯并呋喃上，形成一个新的CC键。使用硝基吲哚1和烯胺2a时，以完全区域和非对映体选择性的方式发生了前所未有的脱芳香化甲醛反应。使用3-硝基苯并呋喃10和烯胺2d时，反应过程不同，并导致生成二烯基苯酚。

更新日期：2016-01-12

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