Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones

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Title:Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones
Creators:
Šimo, Ondrej
Rybár, Alfonz
Alföldi, Juraj
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 3, pp. 407-415
Uncontrolled Keywords:Imidazo[1,2,3-<i>cd</i>]purines, Xanthine derivatives, 3,9-Annelated purines, Acyclic nucleoside analogues

Abstract

New 4-alkyl- or 4-phenyl-7-methyl-1,2-dihydro-7<i>H</i>-imidazo[1,2,3-<i>cd</i>]purine-6,8-diones <strong>1</strong> were obtained by intramolecular alkylation of 8-alkyl- or 8-phenyl-9-(2-mesyloxyethyl)-1-methyl-9<i>H</i>-purine-2,6(1<i>H</i>,3<i>H</i>)-diones <strong>5</strong>. The necessary compounds <strong>5</strong> were prepared from 6-[(2-hydroxyethyl)- amino]-3-methyl-5-nitrosopyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione (<strong>2</strong>), which was hydrogenated to 5-amino-6-[(2-hydroxyethyl)amino]-3-methyl derivative <strong>3</strong>; consecutive reactions of the latter with an orthocarboxylate and mesyl chloride afforded 8-alkyl- or 8-phenyl-9-(2-hydroxyethyl)-1-methyl-9<i>H</i>-purine- 2,6(1<i>H</i>,3<i>H</i>)-diones <strong>4</strong> and compounds <strong>5</strong>, respectively.

Title:Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones
Creators:
Šimo, Ondrej
Rybár, Alfonz
Alföldi, Juraj
Uncontrolled Keywords:Imidazo[1,2,3-<i>cd</i>]purines, Xanthine derivatives, 3,9-Annelated purines, Acyclic nucleoside analogues
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:63
Number:3
Page Range:pp. 407-415
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980407UNSPECIFIED
ID Code:1308
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Šimo, Ondrej; Rybár, Alfonz; Alföldi, Juraj (1998) Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones. Collection of Czechoslovak Chemical Communications, 63 (3). pp. 407-415. ISSN 0010-0765

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