Issue 47, 2012

Synthesis of pyrazolo[5,1-a]isoquinolines via silver(i)–rhodium(i) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with cycloprop-2-ene-1,1-dicarboxylate

Abstract

A tandem reaction between N′-(2-alkynylbenzylidene)hydrazide and cycloprop-2-ene-1,1-dicarboxylate co-catalyzed by silver triflate and tris(triphenylphosphine)rhodium chloride is reported. The reaction proceeds through 6-endo-cyclization, [3 + 2] cycloaddition, cyclopropane opening, and aromatization, leading to pyrazolo[5,1-a]isoquinolines in moderate to good yields.

Graphical abstract: Synthesis of pyrazolo[5,1-a]isoquinolines via silver(i)–rhodium(i) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with cycloprop-2-ene-1,1-dicarboxylate

Supplementary files

Article information

Article type
Paper
Submitted
27 Jun 2012
Accepted
11 Oct 2012
First published
12 Oct 2012

Org. Biomol. Chem., 2012,10, 9447-9451

Synthesis of pyrazolo[5,1-a]isoquinolines via silver(I)–rhodium(I) cooperative catalysis in the reaction of N′-(2-alkynylbenzylidene)hydrazide with cycloprop-2-ene-1,1-dicarboxylate

L. Yao, X. Yu, C. Mo and J. Wu, Org. Biomol. Chem., 2012, 10, 9447 DOI: 10.1039/C2OB26824H

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