Synthesis and Chemical Reactivity of New Azaenamines Incorporated the 4,5,6,7-Tetrahydrobenzo[b]thiophene Moiety: 3+3 Atom Combination

被引:46
作者
Abdelhamid, Ismail Abdelshafy [1 ,2 ]
Darwish, Elham Sayed [1 ]
Nasra, Miead Adel [1 ]
Abdel-Gallil, Fathy Mohamed [1 ]
Fleita, Daisy Hanna [3 ]
机构
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
[2] Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
[3] Amer Univ Cairo, Dept Chem, Cairo, Egypt
来源
SYNTHESIS-STUTTGART | 2010年 / 07期
关键词
azaenamine; tetrahydrobenzo[b]thiophene; Michael addition; condensation; Mannich alkylation; MANNICH-TYPE REACTION; DERIVATIVES; PYRIDAZINES; CHITOSAN; CATALYST; AMINES; ACID;
D O I
10.1055/s-0029-1219235
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel azaenamines incorporating a tetrahydrothiophene moiety were prepared. Michael addition of an azaenamine with alpha,beta-unsaturated nitriles took place to give [1]benzothieno[3',2':5,6]pyrimido[1,2-b]pyridazine (thia- triaza-benzo[a]fluorene) derivatives. The condensation with malononitrile resulted in the formation of a [1]benzothieno[3',2':5,6]pyrimido[1,2-b]pyridazine-4-carbonitrile. The azaenamine also reacted with aldehydes and piperidine to give Mannich products.
引用
收藏
页码:1107 / 1112
页数:6
相关论文
共 16 条
[11]  
REINHARD R, 1999, Patent No. 9914201
[12]   The use of 4-(3,4-dichlorophenyl)-4-oxo-2-(4-antipyrinyl)-butanoic acid in the preparation of some new heterocyclic compounds with expected biological activity [J].
Sayed, GH ;
Hamed, AA ;
Meligi, GA ;
Boraie, WE ;
Shafik, M .
MOLECULES, 2003, 8 (03) :322-332
[13]  
Shi M, 2005, TETRAHEDRON, V61, P4965, DOI 10.1016/j.tet.2005.03.059
[14]   ONE POT SYNTHESIS OF 3-AMINO-1H-PYRAZOLE-4-CARBONITRILE [J].
WOLFBEIS, OS .
MONATSHEFTE FUR CHEMIE, 1981, 112 (6-7) :875-877
[15]   Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid [J].
Wu, Hui ;
Shen, Yang ;
Fan, Li-yan ;
Wan, Yu ;
Zhang, Pu ;
Chen, Cai-fa ;
Wang, Wen-xiang .
TETRAHEDRON, 2007, 63 (11) :2404-2408
[16]  
1999, Patent No. 9921859