Synfacts 2008(4): 0351-0351  
DOI: 10.1055/s-2008-1042854
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Biradical Cylization Route to Axially Chiral Biheteroaryls

Contributor(s): Victor Snieckus, Erhad Ascic
M. AlajarÍn*, B. Bonillo, A. Vidal*, D. Bautista
Universidad de Murcia, Spain
Further Information

Publication History

Publication Date:
19 March 2008 (online)

Significance

Reported is the synthesis of axially chiral bis(benzocarbazoles) 3 and bis(quinindolines) 4 via two independent biradical cyclizations from bis(ketenimines) 1 and bis(carbodiimides) 2, which in turn are derived from the 1,4-diphenyl-1,3-butadiynes.The preparation of mixed bi­hetero­aryls, consisting of benzocarbazole and quinindoline units, is also reported with a slightly modified strategy. The scope of this interesting multibond-forming reaction was poorly investigated. A mechanism for cyclization is proposed involving biradical intermediate A.