synthesis of n-7-substituted purines from imidazole precursors从咪唑前体的合成n-7-substituted嘌呤.pdfVIP

Molecules 1999, 4, 287-309 molecules ISSN 1420-3049 Synthesis of N-7-Substituted Purines from Imidazole Precursors Stanislaw Ostrowski Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, Poland Fax: (+48)-22-6326681, E-mail: stan@.pl Received: 23 February 1999 / Accepted: 4 June 1999 / Published: 25 September 1999 Abstract: Synthesis of purines and purine mono-1-oxides from the respective 5-substituted 4-nitroimidazole derivatives is described. The commercially available 4-nitroimidazole, in a few simple steps (including Vicarious Nucleophilic Substitution of Hydrogen), was transformed into: 4-aminoimidazoyl-5-carboximes, N-[1-(4-amino-1H-imidazol-5- yl)methylidene]-N-(aryl)amine derivatives or into 4-amino-5-aminomethyl-imidazole. These intermediates were cyclized to the final products. O N N O N N 2 VNS 2 PURINES N Y N R R Keywords: purines, purine N-oxides, nitroimidazoles, oximes, Schiff bases, isocyanides, Vicarious Nucleophilic Substitution. 1. Introduction In the past years we have reported new and efficient approaches to fused pyrimidines [1-3], using aromatic nitrocompounds which were commercially or very readily available as starting materials. In these publications, the synthesis of many fused pyrimidines based on carbocy