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Synfacts 2006(3): 0201-0201  
DOI: 10.1055/s-2006-931964
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pyrrolidinyl, Pyrazolidinyl, and Isoxazolidinyl Isoquinolines

Contributor(s): Victor Snieckus, Oleg M. Demchuk
H. A. Dondas, C. W. G. Fishwick, X. Gai, R. Grigg*, C. Kilner, N. Dumrongchai, B. Kongkathip, N. Kongkathip, C. Polysuk, V. Sridharan
Leeds University, UK; kasetsart University, Bangkok, Thailand; Mersin University, Turkey
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

An innovative cascade synthesis of complex heterocycles, involving a Pd-catalyzed allene coupling, heteroannulation and terminating with a 1,3-dipolar cycloaddition is reported. This sequence was postulated to proceed, for the reaction with amino esters, via intermediate B rather then A, providing pyrrolidinyl, pyrazolidinyl, and isoxazolidinyl isoquinolines, resulting in substantial increase in molecular complexity with the formation of five new bonds, two rings and two to four ste­reocenters with good regio- and stereoselectivity. Mechanistic considerations are proposed.