A new and efficient approach to the synthesis of 6-amidino-2-oxopurines

• Type: Article in International Scientific Journal
• Date: 2001

Authors

Booth, BL (Author) Other; Cabral, IM (Author) Other; Dias, AM (Author) Other; Victor de Freitas (Author) FCUP; Beja, AMM (Author) Other; Proenca, MF (Author) Other; Silva, MR (Author) Other

Journal

Title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1

Pages: 1241-1251

ISSN: 1472-7781

Publisher: ROYAL SOC CHEMISTRY

Indexing

ISI Web of Knowledge - 22 Citations

Scopus - 29 Citations

Other information

Authenticus ID: P-000-XE8

DOI: 10.1039/b010224p

Abstract (EN): The reaction of 5-amino-4-cyanoformimidoylimidazoles 1a and 1b with tosyl isocyanate proved to be a mild and efficient method for the synthesis of the corresponding 6-amidino-2-oxopurines 5. These compounds, which were isolated in almost quantitative yield, rearrange in the presence of acetic acid-DMF to give a pyrimido[5,4-d]pyrimidin-2-one 6. The structure of compound 6 was confirmed by X-ray crystallography. The pathway for both reactions is discussed. Studies on the reactivity of tosyl isocyanate with imidazoles 2, 7, 8 and 16, obtained from 1 by selective acylation of the amino or imino nitrogen atoms, enabled clarification of the mechanism for purine formation.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11