A New Synthetic Approach to Pyrrolo[3,4-a]indolizines

Alexander D. Tereshchenko; Dmitry A. Sysoiev; Anton V. Tverdokhlebov; Andrey A. Tolmachev

doi:10.1055/s-2005-918510

PAPER

A New Synthetic Approach to Pyrrolo[3,4-a]indolizines

Alexander D. Tereshchenko^a, Dmitry A. Sysoiev^b, Anton V. Tverdokhlebov*^a, Andrey A. Tolmachev^b
^a Enamine Ltd., Alexandra Matrosova str. 23, 01103 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: atver@univ.kiev.ua;
^b Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033 Kiev, Ukraine

Abstract

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Abstract

2-Pyridineacetonitrile was found to react with 1,3-dichloro-2-propanone in the presence of chlorotrimethylsilane yielding 2-chloromethyl-1-indolizinecarbonitrile. The chlorine atom in the prepared indolizine was replaced by various nucleophiles including substituted anilines. Treatment of 2-(arylamino)methyl-1-indolizinecarbonitriles with hydrochloric acid resulted in 2-aryl-2,3-dihydro-1H-pyrrolo[3,4-a]indolizine-1-iminium chlorides.

Key words

alkylations - amidines - chlorotrimethylsilane - nitriles - ultrasound

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