Selective N1-alkylation of pyrimidine bases via radical (S(RN)1) mechanism

Article abstract of DOI:10.1080/15257779408011887

Under photostimulated S(RN)1 conditions the cytosine nitranion behaves as a nucleophile toward the carbon radical generated from gem halonitro, or gem dinitroalcane derivatives to give regiospecifically the N-1 alkyled cytosine compound which is representative of a new series of cytosine acyclonucleosides. Uracile and its 5-fluoro or 5-nitro analogs fail to react and thymine gives an unexpected disubstituted S(RN)1 product whose formation is discussed.

Full text of DOI:10.1080/15257779408011887

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Nucleosides and Nucleotides
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Selective N1-Alkylation of Pyrimidine
Bases via Radical (SRN1) Mechanism
Rachid Benhida a , Tawfik Gharbaoui a , Andre Lechevallier a & Rene
Beugelmans a
a Institut de Chimie des Substances Naturelles, CNRS , Gif sur
Yvette, 91190, France
Published online: 24 Sep 2006.
To cite this article: Rachid Benhida , Tawfik Gharbaoui , Andre Lechevallier & Rene Beugelmans
(1994) Selective N1-Alkylation of Pyrimidine Bases via Radical (SRN1) Mechanism, Nucleosides and
Nucleotides, 13:5, 1169-1177, DOI: 10.1080/15257779408011887
To link to this article: http://dx.doi.org/10.1080/15257779408011887
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