Reaction of acetophenone and benzylphenylketone oximes with phenylacetylene: a route to di- and triphenylpyrroles

被引：11

作者：

Petrova, Ol'ga V. ^{[1
]}

Sobenina, Luybov' N. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

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

Hyun, Sang Heon ^{[2
]}

Trofimov, Boris A. ^{[1
]}

机构：

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

[2] Samsung Adv Inst Technol, Display Device & Mat Lab, Yongin 446712, Gyeonggi Do, South Korea

来源：

ARKIVOC | 2009年

关键词：

Acetophenone oxime; benzylphenylketoxime; phenylacetylene; 2,5-diphenyl-1H-pyrrole; 2,3,4-and 2,3,5-triphenyl-1H-pyrroles; EFFICIENT SYNTHESIS; PYRROLES; KETOXIMES;

D O I：

10.3998/ark.5550190.0010.402

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of oximes of aromatic ketones with phenylacetylene in the presence of superbase systems (MOH-DMSO, where M = Li, Na, K) has been extensively studied for the first time. The effects of alkaline metal cation, the ketoximes structure and the reaction conditions (temperature, duration) on the products composition have been evaluated. Acetophenone oxime reacts with phenylacetylene (MOH-DMSO, where M = Li, Na, K, 140 degrees C, 6 h) to afford 2,5-diphenyl-1H- pyrrole in 14-18% isolated yield. The reaction of benzylphenylketoxime with phenylacetylene (LiOH-DMSO, 120 degrees C, 12 h) delivers 2,3,4-, 2,3,5-triphenyl-1H-pyrroles (in 17% total yield) and 2,3,4-triphenyl-1-[(Z)-2-phenylethenyl]-1H-pyrrole (7% yield).

引用

页码：14 / 20

页数：7

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