Issue 23, 2003
From the journal:

Organic & Biomolecular Chemistry

Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

Valery K. Brel,*a   Vitaly K. Belsky,b   Adam I. Stash,b   Valery E. Zavodnikb  and  Peter J. Stangc  

* Corresponding authors

a Institute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka, Moscow Region, 142432, Russian Federation
E-mail: brel@ipac.ac.ru
Fax: 7(095)7857024

b L. Karpov of Institute of Physical-Chemistry, 105064, Moscow, Russian Federation

c Department of Chemistry, University of Utah, Salt Lake City, UT 84112, USA

Abstract

Reaction of 1-chloro-4-(diethoxyphosphonyl)alka-2,3-dienes 14,15 with purine and pyrimidine heterocyclic bases in the presence of cesium carbonate afforded new acyclic analogues of nucleotides containing a 1,2-alkadienic skeleton 18–23. Dealkylation of 18–23 furnished phosphonic acids 2a–f. In contrast, alkylation reaction with 1-chloro-4-(diethoxyphosphonyl)octa-2,3-diene 16 led to Z- and E- 1,3-alkadienic phosphonates 25a,b and 26a,b. A similar reaction with 1-chloro-4-(diethoxyphosphonyl)-2-methylbuta-2,3-diene 17 led to the elimination of hydrochloride and formation of 4-(diethylphosphonyl)-2-methylbut-1-en-3-yne 24. Molecular structures of new acyclic nucleotides 18 and 2f are determined by X-ray crystallographic analysis.

Graphical abstract: Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

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Article information

DOI
https://doi.org/10.1039/B309684J
Article type
Paper
Submitted
15 Aug 2003
Accepted
06 Oct 2003
First published
27 Oct 2003

Org. Biomol. Chem., 2003,1, 4220-4226

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Synthesis and molecular structure of new acyclic analogues of nucleotides with a 1,2-alkadienic skeleton

V. K. Brel, V. K. Belsky, A. I. Stash, V. E. Zavodnik and P. J. Stang, Org. Biomol. Chem., 2003, 1, 4220 DOI: 10.1039/B309684J

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