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Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides

Purines. LXIV. Syntheses of 9-Methyl-2-azaadenine 1-Oxide, Its O-Methyl Derivative, and 1-Substituted 5-Azidoimidazole-4-carboxamides

Authors :
Satoshi Nakajima
Tohru Saito
Yayoi Asahi
Tozo Fujii
Source :
Chemical and Pharmaceutical Bulletin. 42:2263-2268
Publication Year :
1994
Publisher :
Pharmaceutical Society of Japan, 1994.

Abstract

Diazotization of 5-amino-N'-methoxy-1-methylimidazole-4-carboxamidine (4a) with NaNO 2 in 1N aqueous HCI was found to give the 1-methoxy-2-azaadenine derivative 8a HI, which produced 5-azido-1-methylimidazole-4-carbonitrile (5a) on treatment with aqueous Na 2 CO 3 . The ribosyl analogue 5b, obtained from the riboside 4b by similar diazotization, was utilized for the synthesis of 5-azido-1-β-D-ribofuranosylimidazole-4-carboxamide (9b), a novel AICA riboside analogue. On heating in HCONMe 2 at 70°C for 10 min, 8a.HI yielded the 1-N-oxide 7a. Several reactions to transform the functional groups in 5a were also investigated.

Details

ISSN :
13475223 and 00092363
Volume :
42
Database :
OpenAIRE
Journal :
Chemical and Pharmaceutical Bulletin
Accession number :
edsair.doi...........c27a3711bfe1ece86fcb756407078b14
Full Text :
https://doi.org/10.1248/cpb.42.2263