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

Xingxin Yu; Guanyinsheng Qiu; Jianping Liu; Jie Wu

doi:10.1055/s-0030-1260063

SPECIALTOPIC

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

Xingxin Yu^a, Guanyinsheng Qiu^a, Jianping Liu*^b, Jie Wu*^a
^a Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China
Fax: +86(21)65641740; e-Mail: jie_wu@fudan.edu.cn;
^b EENT Hospital, Fudan University, 83 Fenyang Road, Shanghai 200031, P. R. of China

Abstract

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Abstract

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.

Key words

2-alkynylbenzaldehydes - dimethyl cyclopropane-1,1-dicarboxylate - nickel perchlorate hexahydrate - silver(I) triflate - sulfonohydrazide

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