Pyrrolidine analogues of 2′,3′-dideoxynucleosides: synthesis via 9-aminopurines and 1-aminopyrimidines

Abstract

Analogues of 2′,3′-dideoxynucleosides in which the tetrahydrofuran ring is replaced by a pyrrolidine ring linked to the base through an N–N bond have been prepared. The adenine 26, guanine 25 and hypoxanthine 27 compounds were synthesised via 9-aminopurines. Corresponding derivatives of 5-iodouracil 31, 5-chlorouracil 33 and 5-chlorocytosine 35 were prepared by substitution at the 5-position of hydroxy protected uracil derivatives. Enantiomers, 40a and 40b, of the pyrrolidine analogue of dideoxycytidine were prepared from 1-aminocytosine. The novel N-aminobases 9-aminoadenine 10, 1-aminocytosine 13 and 1-aminothymine 15 are described.