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Synfacts 2007(7): 0685-0685  
DOI: 10.1055/s-2007-968682
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Benzimidazolium Salts from Dihydropyridines and Isocyanides

Contributor(s): Victor Snieckus, Jignesh J. Patel
C. Masdeu, E. GÓmez, N. A. O. Williams, R. Lavilla*
Institute for Research In Biomedicine, Barcelona Science Park and University of Barcelona, Spain
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

Described is a one-pot synthetic procedure for benzimidazolium salts from dihydropyridines and isocyanides. This 3-CR sequence consists of a formal double-bond insertion of two isocyanides into the electron-rich dihydropyridine ring to give an intermediate which, upon rearrangement, leads to products in which the formation of three C-C bonds and one C-N bond has occurred. The same reaction sequence using bromine, as shown, has been reported to give substituted tetrahydropyridines (R. Lavilla et al. QSAR Comb. Sci. 2006, 25, 465-473).