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Synthesis 2006(2): 349-353  
DOI: 10.1055/s-2005-918510
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Alexander D. Tereshchenkoa, Dmitry A. Sysoievb, Anton V. Tverdokhlebov*a, Andrey A. Tolmachevb
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
Further Information

Publication History

Received 29 June 2005
Publication Date:
21 December 2005 (online)

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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