Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines

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Title:Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines
Creators:
Hocková, Dana
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 2, pp. 247-258
Uncontrolled Keywords:Hydrogenation, Acyclic nucleoside phosphonates, Pyrimidines, Nucleosides, Nucleotide analogues, Antivirals, Alkynes, Cross-coupling reactions, Sonogashira reaction

Abstract

Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity. <p>

Title:Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines
Creators:
Hocková, Dana
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Hydrogenation, Acyclic nucleoside phosphonates, Pyrimidines, Nucleosides, Nucleotide analogues, Antivirals, Alkynes, Cross-coupling reactions, Sonogashira reaction
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:2
Page Range:pp. 247-258
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20050247UNSPECIFIED
ID Code:2356
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:18

Citation

Hocková, Dana; Masojídková, Milena; Holý, Antonín (2005) Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines. Collection of Czechoslovak Chemical Communications, 70 (2). pp. 247-258. ISSN 0010-0765

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