Affiliation:
1. Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry and Biochemistry, University of Guelph, Guelph, ON N1G 2W1, Canada.
Abstract
Dipolar cycloaddition reactions allow for the efficient construction of five-membered heterocycles, often with diverse medicinal applications. We examined the 1,3-dipolar cycloaddition of 7-oxabenzonorbornadienes and 7-azabenzonorbornadienes with acetonitrile oxide and benzonitrile oxide, achieving an assortment of heterobicycle-fused isoxazolines with good to excellent yields. All isoxazolines were consistently directed to the exo face of the bicyclic framework with complete stereoselectivity. Preliminary biological testing of the adducts also showed positive anti-cancer activity, suggesting their potential pharmaceutical utility.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
11 articles.
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