N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction

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Title:N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction
Creators:
Havelková, Martina
Studenovský, Martin
Dvořák, Dalimil
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 5, pp. 797-804
Uncontrolled Keywords:Thallium acetate, Michael additions, Purines, Hypoxanthines, Heck reaction, Palladium

Abstract

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded <i>N</i><sup>1</sup>-alkylhypoxanthine derivatives. Formation of these unexpected products can be rationalised as a Tl<sup>+</sup>- or Ag<sup>+</sup>-assisted substitution of halogen with acetate anion. The 6-acetoxypurine derivative thus formed then eliminates ketene and gives 7-benzyl- or 9-benzylhypoxanthine. Conjugate addition of these compounds onto Michael acceptors furnishes the <i>N</i><sup>1</sup>-substituted hypoxanthine derivatives. <p>

Title:N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction
Creators:
Havelková, Martina
Studenovský, Martin
Dvořák, Dalimil
Uncontrolled Keywords:Thallium acetate, Michael additions, Purines, Hypoxanthines, Heck reaction, Palladium
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:65
Number:5
Page Range:pp. 797-804
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000797UNSPECIFIED
ID Code:1680
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Havelková, Martina; Studenovský, Martin; Dvořák, Dalimil (2000) N1-Substituted Hypoxanthine Derivatives from the Reaction of 6-Halopurines with Michael Acceptors Under the Conditions of Heck Reaction. Collection of Czechoslovak Chemical Communications, 65 (5). pp. 797-804. ISSN 0010-0765

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