Synthesis of 2,3,4,11b-Tetrahydro-1H-pyridazino[6,1-a]isoquinolines via the Three-Component Reaction of 2-Alkynylbenzaldehydes, a Sulfonohydrazide and Dimethyl Cyclopropane-1,1-dicarboxylate

被引：12
|
作者：
Yu, Xingxin [2 ]
Qiu, Guanyinsheng [2 ]
Liu, Jianping [1 ]
Wu, Jie [2 ]
机构：
[1] Fudan Univ, EENT Hosp, Shanghai 200031, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
来源：
SYNTHESIS-STUTTGART | 2011年 / 14期
基金：
中国国家自然科学基金;
关键词：
2-alkynylbenzaldehydes; dimethyl cyclopropane-1,1-dicarboxylate; nickel perchlorate hexahydrate; silver(I) triflate; sulfonohydrazide; DONOR-ACCEPTOR CYCLOPROPANES; HIGHLY DIASTEREOSELECTIVE SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; REISSERT-TYPE REACTION; ORGANIC-SYNTHESIS; ACTIVATED CYCLOPROPANES; CYCLOADDITION REACTIONS; DIPOLAR CYCLOADDITION; DERIVATIVES; NITRONES;
D O I：
10.1055/s-0030-1260063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-component reaction of 2-alkynylbenzaldehydes, a sulfonohydrazide and dimethyl cyclopropane-1,1-dicarboxylate, co-catalyzed by silver(I) triflate and nickel(II) perchlorate hexahydrate, is described, which affords 2,3,4,11b-tetrahydro-1H-pyridazino[6,1-a]isoquinolines in moderate to good yields. A possible reaction pathway that proceeds via a tandem 6-endo-cyclization and [3+3] cycloaddition sequence is proposed.
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页码：2268 / 2274
页数：7
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