Expedient one-step synthesis of nitrogen stilbene analogs by transition metal-free hydroamination of arylacetylenes with pyrroles

被引：16

作者：

Dvorko, Marina Yu ^{[1
]}

Schmidt, Elena Yu ^{[1
]}

Glotova, Tatyana E. ^{[1
]}

Shabalin, Dmitrii A. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Kobychev, Vladimir B. ^{[2
]}

Petrushenko, Konstantin B. ^{[1
]}

Mikhaleva, Al'bina I. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

[2] Irkutsk State Univ, Inst Math Econ & Informat Sci, Irkutsk 664003, Russia

来源：

TETRAHEDRON | 2012年 / 68卷 / 07期

关键词：

Pyrroles; Styrylpyrroles; Nucleophilic addition; Superbase; Isomerization; SUBSTITUTED STILBENES; N-VINYLPYRROLES; RESVERATROL; VINYLATION; AZOLES; HYPERPOLARIZABILITIES; DERIVATIVES; ALKENES; ALKYNES;

D O I：

10.1016/j.tet.2011.12.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel family of nitrogen stilbene analogs, 1-styrylpyrroles, has been synthesized in good to excellent yields by a straightforward facile transition metal-free addition of pyrroles to arylacetylenes in the KOH/DMSO system (90-120 degrees C, 5-13 h). Thermodynamically controlled E/Z-isomer ratio of 1-styrylpyrroles depends on structure of both pyrroles and acetylenes ranging from ca. 100% E-stereoselectivity (for the pair unsubstituted pyrrole phenylacetylene) to 90, 96% Z-stereoselectivity (for the pairs: 2-phenylpyrrole-phenylacetylene and 2-(2-thienyl)pyrrole-phenylacetylene, respectively). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1963 / 1971

页数：9

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