Synthesis of multisubstituted furans, pyrroles, and thiophenes via ynolates

被引:91
作者
Shindo, Mitsuru [1 ]
Yoshimura, Yutaka
Hayashi, Maiko
Soejima, Hiroe
Yoshikawa, Takashi
Matsumoto, Kenji
Shishido, Kozo
机构
[1] Kyushu Univ, Inst Mat Chem & Engn, Kasuga, Fukuoka 8168580, Japan
[2] Kyushu Univ, Interdisciplinary Grad Sch Engn Sci, Kasuga, Fukuoka 8168580, Japan
[3] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
关键词
D O I
10.1021/ol0705200
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthetic method for the preparation of multisubstituted furans, thiophenes, and pyrroles using ynolates was developed. This novel formal [4 + 1] annulation by C2-C3 and C3-C4 bond formations includes cycloaddition, cyclization, decarboxylation, and dehydration as key steps.
引用
收藏
页码:1963 / 1966
页数:4
相关论文
共 37 条
[1]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[2]   Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].
Bharadwaj, AR ;
Scheidt, KA .
ORGANIC LETTERS, 2004, 6 (14) :2465-2468
[3]   Synthesis of highly substituted pyrroles via a multimetal-catalyzed rearrangement-condensation-cyclization Domino approach [J].
Binder, JT ;
Kirsch, SF .
ORGANIC LETTERS, 2006, 8 (10) :2151-2153
[4]   Palladium-catalyzed multicomponent coupling of alkynes, imines, and acid chlorides: A direct and modular approach to pyrrole synthesis [J].
Dhawan, R ;
Arndtsen, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (02) :468-469
[5]   Synthesis of the pyrrole-imidazole alkaloids [J].
Hoffmann, H ;
Lindel, T .
SYNTHESIS-STUTTGART, 2003, (12) :1753-1783
[6]   Regioselective syntheses of substituted furans [J].
Hou, XL ;
Cheung, HY ;
Hon, TY ;
Kwan, PL ;
Lo, TH ;
Tong, SY ;
Wong, HNC .
TETRAHEDRON, 1998, 54 (10) :1955-2020
[7]   Phosphine-mediated reductive condensation of γ-acyloxy butynoates:: A diversity oriented strategy for the construction of substituted Furans [J].
Jung, CK ;
Wang, JC ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4118-4119
[8]   Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst [J].
Kamijo, S ;
Kanazawa, C ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9260-9266
[9]  
KATRIZKY AR, 1996, COMPREHENSIVE HETE 2, V2
[10]   A novel Cu-assisted cycloisomerization of alkynyl imines: Efficient synthesis of pyrroles and pyrrole-containing heterocycles [J].
Kel'in, AV ;
Sromek, AW ;
Gevorgyan, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :2074-2075