3,4-diazanorcaradienes and 4,5-dihydropyridazines as precursors for new stable azomethine ylides

被引:7
作者
Böhm, T [1 ]
Elender, K [1 ]
Riebel, P [1 ]
Troll, T [1 ]
Weber, A [1 ]
Sauer, J [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany
关键词
azomethine ylides; diazahomotropilidenes; rearrangement; ring transformation;
D O I
10.1016/S0040-4020(99)00516-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a new class of stable coloured azomethine ylides 3 derived from 3,4-diazanorcaradienes is reported, which under acid catalysis are transformed to again coloured stable azomethine ylides 4 containing a five-membered 1-aza-1,3-cyclopentadiene skeleton. Azomethine ylides 3 in boiling methanol rearrange to 3,5-diazahomotropilidenes 8 in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9515 / 9534
页数:20
相关论文
共 17 条
[1]  
[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[2]  
BOHM T, 1999, UNPUB TETRAHEDRON
[3]   Dicyano(7,7-dimethyl-2,5-di-p-tolyl-3,4-diazabicyclo[4.1.0]hepta-2,4-dien-3-ium-3-yl)methanide and (4-benzoyl-5,5-dimethyl-2-phenyl-1-azacyclopenta-1,3-dien-1-ium-1-yl)dicyanomethanide, two stable azomethine ylides [J].
Breu, J ;
Range, KJ ;
Riebel, P ;
Weber, A ;
Sauer, J .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 :2053-2056
[4]  
Grashey R., 1984, 1 3 DIPOLAR CYCLOADD, P733
[5]  
Grigg R., 1993, ADV CYCLOADDITION, V3, P161
[6]  
KANEMASA S, 1993, ADV CYCLOADDIT, V3, P99
[7]  
KANEMASA S, 1993, ADV CYCLOADDITION
[8]   TETRACYANOETHYLENE OXIDE .I. PREPARATION AND REACTION WITH NUCLEOPHILES [J].
LINN, WJ ;
WEBSTER, OW ;
BENSON, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (16) :3651-&
[9]  
MAIER A, 1994, THESIS U REGENSBURG
[10]  
REIBEL P, 1996, THESIS U REGENSBURG