Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy

被引:201
作者
Bharadwaj, AR [1 ]
Scheidt, KA [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
关键词
D O I
10.1021/ol049044t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A multicomponent synthesis of highly substituted pyrroles catalyzed by thiazolium salts has been disclosed. The reaction employs an acyl anion conjugate addition reaction of acylsilanes (sila-Stetter) and unsaturated ketones to generate 1,4-dicarbonyl compounds in situ. The subsequent addition of various amines promotes a Paal-Knorr reaction, affording the desired pyrrole nucleus in an efficient one-pot process.
引用
收藏
页码:2465 / 2468
页数:4
相关论文
共 46 条
[1]   INTERMEDIATES IN THE PAAL-KNORR SYNTHESIS OF PYRROLES [J].
AMARNATH, V ;
ANTHONY, DC ;
AMARNATH, K ;
VALENTINE, WM ;
WETTERAU, LA ;
GRAHAM, DG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6924-6931
[2]  
[Anonymous], 1994, CURR TOP ELECTROCHEM
[3]   Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].
Boger, DL ;
Boyce, CW ;
Labroli, MA ;
Sehon, CA ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62
[4]   Newly designed acylsilanes as versatile tools in organic synthesis [J].
Bonini, BF ;
Comes-Franchini, M ;
Fochi, M ;
Mazzanti, G ;
Ricci, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 567 (1-2) :181-189
[5]   A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence [J].
Braun, RU ;
Zeitler, K ;
Muller, TJJ .
ORGANIC LETTERS, 2001, 3 (21) :3297-3300
[7]   THE THIAZOLIUM CATALYZED BENZOIN CONDENSATION WITH MILD BASE DOES NOT INVOLVE A DIMER INTERMEDIATE [J].
BRESLOW, R ;
KIM, R .
TETRAHEDRON LETTERS, 1994, 35 (05) :699-702
[8]   The mechanism of thiazolium catalysis [J].
Breslow, R ;
Schmuck, C .
TETRAHEDRON LETTERS, 1996, 37 (45) :8241-8242
[9]   MECHANISM OF ALPHA-SILYLCARBINOL TO SILYL ETHER REARRANGEMENT [J].
BROOK, AG ;
LEGROW, GE ;
MACRAE, DM .
CANADIAN JOURNAL OF CHEMISTRY, 1967, 45 (03) :239-&
[10]   REACTIONS OF BENZALDEHYDE WITH THIAZOLIUM SALTS IN ME(2)SO - EVIDENCE FOR INITIAL FORMATION OF 2-(ALPHA-HYDROXYBENZYL)THIAZOLIUM BY NUCLEOPHILIC-ADDITION AND FOR DRAMATIC SOLVENT EFFECTS ON BENZOIN FORMATION [J].
CHEN, YT ;
BARLETTA, GL ;
HAGHJOO, K ;
CHENG, JT ;
JORDAN, F .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7714-7722