General route for the facile synthesis of pyrimidin-2-one-4-thione derivatives via the annulation of cyclic o-aminonitriles using carbonyl sulfide

Abstract

A facile synthesis of 4,5-diamino-9-(j9-D-ribofuranosyl)pyrrolo [2,3-d:5,4-d']dipyrimidin-7-one ( 6) from an appropriately substituted pyrrolo[2,3-d]pyrimidine has been accomplished. A key reaction in this synthesis involves the ring closure of a cyclic o-aminonitrile precursor by using carbonyl sulfide to obtain the versatile 4-thioxopyrimidin-2-one intermediate 3. A study involving the generality of this reagent for the annulation of cyclic o-aminonitriles under different reaction conditions is also discussed.

A Self‐Complementary Nucleoside: Synthesis, Solid‐State Structure, and Fluorescence Behavior

“…Nucleosides with two hydrogen-bonding heads were first reported as anticancer drug candidates. [5] Recently reported doubleheaded nucleosides have an additional nucleobase at various positions of the sugar to stabilize or to expand their secondary structures and to give extra hydrogen-bonding abilities. [6] Abstract: A novel self-complementary nucleoside ( A T), featuring two complementary nucleobases linked through an ethynyl group has been synthesized.…”

“…Although various kinds of dual‐complementary nucleobase derivatives have been reported, there are relatively few nucleoside derivatives. Nucleosides with two hydrogen‐bonding heads were first reported as anticancer drug candidates 5. Recently reported double‐headed nucleosides have an additional nucleobase at various positions of the sugar to stabilize or to expand their secondary structures and to give extra hydrogen‐bonding abilities 6…”