Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines

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Title:Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines
Creators:
Tobrmanová, Miroslava
Tobrman, Tomáš
Dvořák, Dalimil
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 76, 4, pp. 311-326
Uncontrolled Keywords:Heterocycles, Palladium, Nucleophilic substitution

Abstract

C<sup>8</sup>-Alkenylpurines were synthesized starting from purin-8-yl(allyl) acetates using Pd-catalyzed allylic substitution. The described protocol allows, by reaction of purin-8-yl(allyl) acetates with stabilized nucleophiles, an access to novel (<i>E</i>)-8-alkenylpurine derivatives under Pd2dba<sub>3</sub>·CHCl<sub>3</sub> catalysis in dry THF in yields ranging from 31 to 76%. A wide range of nucleophiles showed exclusive <i>E</i>-alkene formation, however, ethyl nitroacetate gave mixture of <i>E/Z</i>-alkenes. On contrary, purin-2-yl(allyl) acetates reacted smoothly only with dimethyl malonate.

Title:Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines
Creators:
Tobrmanová, Miroslava
Tobrman, Tomáš
Dvořák, Dalimil
Uncontrolled Keywords:Heterocycles, Palladium, Nucleophilic substitution
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:76
Number:4
Page Range:pp. 311-326
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2011030UNSPECIFIED
ID Code:6512
Item Type:Article
Deposited On:31 Mar 2011 17:31
Last Modified:31 Mar 2011 15:31

Citation

Tobrmanová, Miroslava; Tobrman, Tomáš; Dvořák, Dalimil (2011) Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines. Collection of Czechoslovak Chemical Communications, 76 (4). pp. 311-326.

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