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A novel synthesis of condensed bicyclic thiopyrimidine glycosides utilising 1H-cyclopentapyrimidine-2(3H)-thiones and alpha-bromoglucose or alpha-bromogalactose tetraacetate as starting components is described.

A series of different novel nonclassical nucleosides have been synthesised and evaluated for their inhibitory activity against human immunodeficiency virus (HIV) replication in MT-4 cells.

Condensation of cyanothioacetamide or cyanoacetamide with sodium salts of 2-formyl-1-cycloalkanones afforded the corresponding cycloalkane ring fused pyridine-2(1H)-thiones and -2-pyridones. The latter compounds served as a key intermediates for the synthesis of a new class of cycloalkane ring fused pyridine glycosides.