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
[31]   Synthetic uses of ynolates [J].
Shindo, Mitsuru .
TETRAHEDRON, 2007, 63 (01) :10-36
[32]   SYNTHESIS OF AMINO-ACIDS AND RELATED COMPOUNDS .7. CONVENIENT SYNTHESIS OF 3-SUBSTITUTED PYRROLE-2,4-DICARBOXYLIC ACID-ESTERS [J].
SUZUKI, M ;
MIYOSHI, M ;
MATSUMOT.K .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) :1980-1980
[33]   CHEMISTRY OF SULFONYLMETHYL ISOCYANIDES .37. SYNTHESIS OF 3,4-DISUBSTITUTED PYRROLES BEARING SUBSTITUENTS OF ELECTRON-WITHDRAWING AND/OR ELECTRON-DONATING NATURE [J].
VANLEUSEN, D ;
VANECHTEN, E ;
VANLEUSEN, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2245-2249
[34]   Biological formation of pyrroles: Nature's logic and enzymatic machinery [J].
Walsh, Christopher T. ;
Garneau-Tsodikova, Sylvie ;
Howard-Jones, Annaleise R. .
NATURAL PRODUCT REPORTS, 2006, 23 (04) :517-531
[35]   Convenient synthesis of polyfunctionalized β-fluoropyrroles from rhodium(II)-catalyzed intramolecular N-H insertion reactions [J].
Wang, YL ;
Zhu, SZ .
ORGANIC LETTERS, 2003, 5 (05) :745-748
[36]   Intramolecular [4+2] cycloaddition reactions of conjugated ynones. Formation of polycyclic furans via the generation and rearrangement of strained heterocyclic allenes [J].
Wills, MSB ;
Danheiser, RL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (36) :9378-9379
[37]   AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones [J].
Yao, TL ;
Zhang, XX ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (36) :11164-11165