Modified Tricyclic Analogues of Acyclovir. A Direct Alkynylation in the Fused Ring

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Title:Modified Tricyclic Analogues of Acyclovir. A Direct Alkynylation in the Fused Ring
Creators:
Zeidler, Joanna
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 8, pp. 1610-1630
Uncontrolled Keywords:Fused purines, Mitsunobu alkylation, Acyclic nucleosides, Reductive deiodination, NH protecting groups, Alkynes, Sonogashira reaction, Acyclovir

Abstract

Two types of new 7-alkynylated tricyclic analogues (3,9-dihydro-5<i>H</i>-imidazo[1,2-<i>a</i>]purin-9-ones) of acyclovir differing by the presence of N-5 substituent, a temporary 2-(4-nitrophenyl)ethyl or a permanent 3-hydroxypropyl were obtained by a Sonogashira coupling. 7-Alk-1-ynyl-5-(3-acetoxypropyl) compounds (<strong>19a</strong>-<strong>19d</strong>, <strong>21a</strong>-<strong>21c</strong>) were efficiently prepared from 7-iodo, 7-iodo-6-methyl precursors <strong>12</strong> and <strong>11</strong>, respectively, and deprotected while the products with unsubstituted N-5 were unstable (e.g. <strong>17</strong>). Iodide <strong>12</strong> was generally less reactive than <strong>11</strong> and underwent a preferable reduction (48%) to deiodinated <strong>8</strong> when coupled with ethynyltrimethylsilane. <p>

Title:Modified Tricyclic Analogues of Acyclovir. A Direct Alkynylation in the Fused Ring
Creators:
Zeidler, Joanna
Uncontrolled Keywords:Fused purines, Mitsunobu alkylation, Acyclic nucleosides, Reductive deiodination, NH protecting groups, Alkynes, Sonogashira reaction, Acyclovir
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:69
Number:8
Page Range:pp. 1610-1630
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041610UNSPECIFIED
ID Code:2298
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Zeidler, Joanna (2004) Modified Tricyclic Analogues of Acyclovir. A Direct Alkynylation in the Fused Ring. Collection of Czechoslovak Chemical Communications, 69 (8). pp. 1610-1630. ISSN 0010-0765

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