Cycloaddition of trifluoromethyl azafulvenium methides: synthesis of new trifluoromethylpyrrole-annulated derivatives

被引：20
作者：
Nunes, Claudio M. [1 ]
Silva, Manuela Ramos [2 ]
Beja, Ana Matos [2 ]
Fausto, Rui [1 ]
Pinho e Melo, Teresa M. V. D. [1 ]
机构：
[1] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal
[2] Univ Coimbra, Dept Phys, P-3004516 Coimbra, Portugal
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 02期
关键词：
Trifluoromethylpyrroles; 1,3-Dipoles; 1,7-Dipoles; Azafulvenium methides; Azomethine ylides; 8 pi+2 pi] Cycloaddition; 1,3-Dipolar cycloaddition; 1,7-Electrocyclization; Microwave; EXTENDED DIPOLAR SYSTEMS; FLASH VACUUM PYROLYSIS; DIAZAFULVENIUM METHIDES; FUNCTIONALIZED PYRROLES; C-VINYLPYRROLES; CHEMISTRY; 5-OXO-5H-PYRROLIZINES; HETEROCYCLES; MUNCHNONES; REACTIVITY;
D O I：
10.1016/j.tetlet.2009.11.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The chemistry of trifluoromethyl azafulvenium methides was explored leading to a new route to trifluoromethylpyrrole-annulated systems. The first evidence of azafulvenium methides acting as 1,3-dipoles is reported. These azafulvenium methides showed site selectivity in the reaction with strong electron-deficient dipolarophiles leading exclusively to 1,3-cycloadducts. In the cycloaddition with less-activated dipolarophiles 1,7-cycloadducts resulting from [8 pi+2 pi] cycloaddition are also formed. FMO analysis of the cycloaddition reactions allowed the rationalization of the observed selectivity. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：411 / 414
页数：4
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