The base 2-carbon of 2',3'-di-O-acetyl-2'-deoxyinosine is strongly activated towards nucleophillic attack when either the 4-nitrophenyl or 2,4-dinitrophenyl group is attached to its N-1 position (product 1 or 2), 1-(omega-Aminoalkyl)- and 1-(omega-hydroxyalkyl)-2'-deoxyinosine derivatives 5, 8-10 have been efficiently synthesized by a rearrangement of the purine ring upon treatment of compound 1 or 2 with the appropriate alpha,omega-diamine or alpha,omega-hydroxyamine. Moreover 1-amino-2'-deoxyinosine 11 and 1-hydroxy-2'-deoxyinosine 13 have been easily prepared in high yields by reaction of substrate 1 or 2, respectively with hydrazine or hydroxylamine.
1-Substituted 2’-deoxyinosine analogues / DE NAPOLI, Lorenzo; A., Messere; Montesarchio, Daniela; Piccialli, Gennaro; Varra, Michela. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - ELETTRONICO. - (1997), pp. 2079-2082. [10.1039/a700987i]
1-Substituted 2’-deoxyinosine analogues
DE NAPOLI, LORENZO;MONTESARCHIO, DANIELA;PICCIALLI, GENNARO;VARRA, MICHELA
1997
Abstract
The base 2-carbon of 2',3'-di-O-acetyl-2'-deoxyinosine is strongly activated towards nucleophillic attack when either the 4-nitrophenyl or 2,4-dinitrophenyl group is attached to its N-1 position (product 1 or 2), 1-(omega-Aminoalkyl)- and 1-(omega-hydroxyalkyl)-2'-deoxyinosine derivatives 5, 8-10 have been efficiently synthesized by a rearrangement of the purine ring upon treatment of compound 1 or 2 with the appropriate alpha,omega-diamine or alpha,omega-hydroxyamine. Moreover 1-amino-2'-deoxyinosine 11 and 1-hydroxy-2'-deoxyinosine 13 have been easily prepared in high yields by reaction of substrate 1 or 2, respectively with hydrazine or hydroxylamine.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
