Intramolecular [4+2] cycloaddition reactions of indolylalkylpyridazines:: synthesis of annulated carbazoles

被引:25
作者
Haider, N [1 ]
Käferbock, J [1 ]
机构
[1] Univ Vienna, Dept Pharmaceut Chem, A-1090 Vienna, Austria
关键词
cycloaddition; indoles; pyridazines; carbazoles;
D O I
10.1016/j.tet.2004.06.008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mono- and bicyclic 1,2-diazines tethered to indole dienophiles by alkylene chains were found to undergo thermally induced intramolecular Diels-Alder reactions with inverse electron demand, affording tetra- and pentacyclic condensed carbazoles. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6495 / 6507
页数:13
相关论文
共 35 条
[1]   OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].
ARTIS, DR ;
CHO, IS ;
JAIMEFIGUEROA, S ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466
[2]   SOME 3-HALOGENOPYRIDAZINES [J].
BARLIN, GB ;
YAP, CY .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (10) :2319-2322
[3]   INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS .3. INTRAMOLECULAR REACTIONS WITH 1,2,4-TRIAZINES TO ACCESS THE CANTHINE SKELETON [J].
BENSON, SC ;
LI, JH ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5285-5287
[4]   INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - 5H-PYRIDAZINO[4,5-B]INDOLES AS CYCLOADDUCTS WITH 3,6-DICARBOMETHOXY-1,2,4,5-TETRAZINE [J].
BENSON, SC ;
PALABRICA, CA ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4610-4614
[5]   Intramolecular inverse electron demand Diels-Alder reactions of tryptamine with tethered heteroaromatic azadienes [J].
Benson, SC ;
Lee, L ;
Yang, L ;
Snyder, JK .
TETRAHEDRON, 2000, 56 (09) :1165-1180
[6]   Inverse electron demand Diels-Alder reactions of indole .5. Reactions of 3-substituted indoles with heteroaromatic azadienes. [J].
Benson, SC ;
Lee, L ;
Snyder, JK .
TETRAHEDRON LETTERS, 1996, 37 (29) :5061-5064
[7]   INDOLE AS A DIENOPHILE IN INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS - REACTIONS WITH 1,2,4-TRIAZINES AND 1,2-DIAZINES [J].
BENSON, SC ;
GROSS, JL ;
SNYDER, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) :3257-3269
[8]   Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system [J].
Bodwell, GJ ;
Li, J .
ORGANIC LETTERS, 2002, 4 (01) :127-130
[9]  
Bodwell GJ, 2002, ANGEW CHEM INT EDIT, V41, P3261, DOI 10.1002/1521-3773(20020902)41:17<3261::AID-ANIE3261>3.0.CO
[10]  
2-K