Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents

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Title:Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents
Creators:
Hocek, Michal
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 1, pp. 136-146
Uncontrolled Keywords:Organotin reagents, Antivirals, Organozinc reagents, Acyclic nucleoside phosphonates, Palladium, PMEA, Phosphonomethoxyethylpurine derivatives

Abstract

The title acyclic nucleotide analogues derived from 6-hetarylpurines were prepared by Pd(0)-catalysed cross-coupling reactions of 9-[2-(diethoxyphosphonylmethoxy)ethyl]-6-iodopurine (<strong>1</strong>) with hetarylorganometallics: (pyridin-2-yl)-, (imidazol-2-yl)- and (pyrrol-2-yl)zinc chlorides or (imidazol-5-yl)- stannanes, followed by deprotection in fair to good yields. The starting 6-iodopurine derivative <strong>1</strong> was prepared by iododeamination of the adenine derivative.

Title:Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents
Creators:
Hocek, Michal
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Organotin reagents, Antivirals, Organozinc reagents, Acyclic nucleoside phosphonates, Palladium, PMEA, Phosphonomethoxyethylpurine derivatives
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:62
Number:1
Page Range:pp. 136-146
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970136UNSPECIFIED
ID Code:1102
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Hocek, Michal; Masojídková, Milena; Holý, Antonín (1997) Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents. Collection of Czechoslovak Chemical Communications, 62 (1). pp. 136-146. ISSN 0010-0765

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