INVERSE-ELECTRON-DEMAND DIELS-ALDER REACTIONS OF CONDENSED PYRIDAZINES .5. 1,4-BIS(TRIFLUOROMETHYL)-PYRIDAZINO[4,5-B]INDOLE AS AN AZADIENE

被引:21
作者
HAIDER, N
WANKO, R
机构
[1] Institute of Pharmaceutical Chemistry, A-1090 Vienna
关键词
D O I
10.3987/COM-94-6726
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The pyridazino[4,5-b]indole (3), which is conveniently available from 3-methylthioindole and the tetrazine (2), undergoes thermally induced inverse-electron-demand Diels-Alder reactions with enamines to afford the cycloalkene-annelated carbazoles (7,8) or the 2-substituted carbazole (9), respectively.
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页码:1805 / 1811
页数:7
相关论文
共 16 条
[1]   HETEROCYCLIC POLYFLUORO-COMPOUNDS .26. SYNTHESIS OF 3,6-BISTRIFLUOROMETHYL-PYRIDAZINES AND 3,6-BISTRIFLOUROMETHYL-DIHYDROPYRIDAZINES [J].
BARLOW, MG ;
HASZELDINE, RN ;
PICKETT, JA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04) :378-380
[2]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[3]   USE OF METHYLTHIOACETALDEHYDE IN SYNTHESIS OF INDOLE AND ITS DERIVATIVES [J].
GASSMAN, PG ;
VANBERGE.TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :591-592
[4]   INTRAMOLECULAR [4+2] CYCLOADDITION REACTIONS OF PYRIDAZINO-[4,5-D]PYRIDAZINES WITH ACETYLENIC SIDE-CHAIN DIENOPHILES - SYNTHESIS OF F-ANNELATED PHTHALAZINES [J].
HAIDER, N ;
LOLL, C .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (02) :357-360
[5]   INVERSE-ELECTRON-DEMAND DIELS-ALDER REACTIONS OF CONDENSED PYRIDAZINES .1. SYNTHESIS OF PHTHALAZINE DERIVATIVES FROM PYRIDAZINO[4,5-D]PYRIDAZINES [J].
HAIDER, N .
TETRAHEDRON, 1991, 47 (24) :3959-3968
[6]   INVERSE-ELECTRON-DEMAND DIELS-ALDER REACTIONS OF CONDENSED PYRIDAZINES .2. SYNTHESIS OF ISOQUINOLINE DERIVATIVES FROM PYRIDO[3,4-D]PYRIDAZINES [J].
HAIDER, N .
TETRAHEDRON, 1992, 48 (35) :7173-7184
[7]  
HARRIS RLN, 1969, TETRAHEDRON LETT, P4465
[8]  
ILLI VO, 1979, SYNTHESIS-STUTTGART, P136
[9]  
KISELYOV AS, 1994, HETEROCYCLES, V37, P775
[10]   THE APPLICATION OF ENAMINES TO A NEW SYNTHESIS OF BETA-KETONITRILES [J].
KUEHNE, ME .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5400-5404