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Synthesis 2007(23): 3683-3691  
DOI: 10.1055/s-2007-990888
PAPER
© Georg Thieme Verlag Stuttgart · New York

Facile Regioselective Synthesis of Pyrazolo[5,1-a]isoquinolines via Ring-Opening Cyclization/Oxidation Reactions of Stable Aroyldiaziridines of 3,4-Tetrahydroisoquinoline with Alkynes

Heriberto Ortega, Sara Ahmed, Howard Alper*
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, ON, K1N 6N5, Canada
Fax: +1(613)5625871; e-Mail: howard.alper@uottawa.ca;
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Publikationsverlauf

Received 16 April 2007
Publikationsdatum:
13. November 2007 (online)

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Abstract

Newly prepared, stable aroyldiaziridines of 3,4-tetrahydroisoquinolines undergo regioselective cycloaddition reactions with a number of both mono and disubstituted alkynes, affording five-membered ring products which, after oxidative aromatization of the pyrazoline ring, lead to the efficient preparation of pyrazolo[5,1-a]isoquinolines. The overall transformation is base-catalyzed and occurs more rapidly in the presence of oxygen, in halogenated solvents and in dioxane.

Key words

isoquinolines - diaziridines - cycloadditions - alkynes - oxidations

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CCDC 643312 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.