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Synfacts 2008(12): 1261-1261
DOI: 10.1055/s-0028-1083607
DOI: 10.1055/s-0028-1083607
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
One-Pot Synthesis of 2-(Indolizin-2-yl)benz-imidazoles from Quinoxalinones
V. A. Mamedov*, D. F. Saifina, A. T. Gubaidullin, A. F. Saifina, I. K. Rizvanov
Kazan Research Center of the Russian Academy of Sciences, Russian Federation
Further Information
Publication History
Publication Date:
20 November 2008 (online)

Significance
Reported is a synthesis of 2-(indolizine-2-yl)benzimidazoles from 3-(2-chloroalkyl)-quinoxazolinones in boiling α-picoline. The proposed mechanism involves an N-alkylation of α-picoline followed by intramolecular cyclization resulting in spiro-compound 2, which was isolated in 10-41% yield depending on the R substituent. Subjection of 2 to further heating results in an intramolecular cyclization-rearrangement to 2-(indolizin-2-yl)benzimidazoles 3 in good preparative yields. The structures of 2 and 3 were confirmed by single-crystal X-ray structure analysis. The scope of this interesting reaction was studied incompletely.