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Synthesis 2011(14): 2268-2274
DOI: 10.1055/s-0030-1260063
DOI: 10.1055/s-0030-1260063
SPECIALTOPIC
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis 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
Further Information
Received
10 March 2011
Publication Date:
09 June 2011 (online)
Publication History
Publication Date:
09 June 2011 (online)
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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