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Synfacts 2007(3): 0250-0250
DOI: 10.1055/s-2007-968259
DOI: 10.1055/s-2007-968259
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Heterocyclic Interconversion. Pyridinium Salts to Indole-3-propenals
A. M. Kearney, C. D. Vanderwal*
University of California, Irvine, USA
Further Information
Publication History
Publication Date:
20 February 2007 (online)


Significance
A new strategy for the synthesis of indole-3-propenals and the corresponding 7-aza series by ring opening of pyridinium salts has been developed. Pyridin-3-yl-2-anilines and the corresponding 2-aminopyridine derivatives, readily prepared by Suzuki cross-couplings, upon treatment with cyanogen bromide in warm ethanol form pyridinium ring-opened intermediates which, upon hydrolysis, afford substituted indole-3-propenals in good yields. The scope of the reaction in terms of R1 and R2 substituents was not sufficiently investigated.