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Synthesis 2009(23): 3967-3974  
DOI: 10.1055/s-0029-1217015
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Some Fluorinated Heteroannulated Pyrimidines - Purine Isosteres - via Inverse-Electron-Demand Diels-Alder Protocol

Viktor O. Iaroshenko*a,b
a ‘Enamine Ltd.’, 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: Yaroshenko@enamine.net ;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv-33, Ukraine
Further Information

Publication History

Received 15 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

The inverse-electron-demand Diels-Alder reaction of electron excessive systems such as enamines, electron-enriched amino heterocycles, and anilines with 2,4,6-tris(polyfluoroalkyl)-1,3,5-triazines was investigated. This study results in the synthesis of a set of polyfluoroalkyl containing pyrimidines, heteroannulated pyrimidines, and quinazolines. Following the elaborated synthetic pathway, l-(β-d-ribofuranosyl)-4,6-bis(polyfluoroalkyl)-1H-pyrazolo[3,4-d]pyrimidines were prepared starting from iso-AIRs.

Key words

pyrimidines - purine isosteres - heterocycles - annulation - fluorine

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