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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2001

Autores

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

Revista

Título: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1

Páginas: 1241-1251

ISSN: 1472-7781

Editora: ROYAL SOC CHEMISTRY

Indexação

ISI Web of Knowledge - 22 Citações

Scopus - 29 Citações

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 11