Palladium-catalyzed cycloisomerization of (Z)-(2-en-4-ynyl)amines:: a new synthesis of substituted pyrroles

被引:40
作者
Gabriele, B [1 ]
Salerno, G [1 ]
Fazio, A [1 ]
Bossio, MR [1 ]
机构
[1] Univ Calabria, Dipartimento Chim, I-87030 Arcavacata Di Rende, Cosenza, Italy
关键词
cycloisomerization; enynamines; palladium; pyrroles;
D O I
10.1016/S0040-4039(00)02206-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(Z)-(2-En-4-ynyl)amines 1 bearing an internal triple bond undergo smooth cycloisomerization into pyrroles 2 in the presence of catalytic amounts of PdCl2 ill conjunction with KCl at 25-100 degreesC in anhydrous N,N-dimethylacetamide. When the triple bond is terminal, spontaneous uncatalyzed cyclization to the corresponding pyrroles takes place. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1339 / 1341
页数:3
相关论文
共 10 条
[1]  
BIRD CW, 1996, COMPREHENSIVE HETERO, V2
[2]   Rapid analogue syntheses of heteroaromatic compounds [J].
Collins, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (17) :2845-2861
[3]   Novel synthesis of substituted thiophenes by palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols [J].
Gabriele, B ;
Salerno, G ;
Fazio, A .
ORGANIC LETTERS, 2000, 2 (03) :351-352
[4]   A general and facile synthesis of substituted furans by palladium-catalyzed cycloisomerization of (Z)-2-En-4-yn-1-ols [J].
Gabriele, B ;
Salerno, G ;
Lauria, E .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) :7687-7692
[5]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20) :2849-2866
[6]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :615-628
[7]   PALLADIUM-CATALYZED CYCLIZATION OF OMEGA-OLEFINIC TOSAMIDES - SYNTHESIS OF NON-AROMATIC NITROGEN-HETEROCYCLES [J].
HEGEDUS, LS ;
MCKEARIN, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (09) :2444-2451
[8]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[9]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF BENZO[B]THIENYLALLYLAMINE ANTIMYCOTICS [J].
NUSSBAUMER, P ;
PETRANYI, G ;
STUTZ, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :65-73
[10]   PYRROLE ANNULATION ONTO ALDEHYDES AND KETONES VIA PALLADIUM-CATALYZED REACTIONS [J].
TROST, BM ;
KEINAN, E .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (14) :2741-2746