Synthesis 2016; 48(15): 2449-2454
DOI: 10.1055/s-0035-1561600
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Cyclopropanated 7-Azabenzonorbornadienes

Emily Carlson
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Email: wtam@uoguelph.ca
,
William Tam*
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada   Email: wtam@uoguelph.ca
› Author Affiliations
Further Information

Publication History

Received: 21 January 2016

Accepted after revision: 08 March 2016

Publication Date:
18 April 2016 (online)


Abstract

7-Azabenzonorbornadienes bearing various aryl or N-substituents were treated with diazomethane in the presence of palladium to afford desirable yields of cyclopropanated products (75–98%). The current approach suggests an efficient synthesis for CH2-cyclopropanated 7-azabenzonorbornadienes which lends promise to the development of new ring-opening preparations of biologically useful organic frameworks.

Supporting Information