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Synthesis 2011(14): 2268-2274  
DOI: 10.1055/s-0030-1260063
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© Georg Thieme Verlag Stuttgart ˙ New York

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 Yua, Guanyinsheng Qiua, 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
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Publikationsverlauf

Received 10 March 2011
Publikationsdatum:
09. Juni 2011 (online)

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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

    Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0014th:
  • Primary Data

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