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

MA Hernandez, FL Chung, RA Earl…

Index: Hernandez, Maria A.; Chung, Fung-Lung; Earl, Robert A.; Townsend, Leroy B. Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 3941 - 3945

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Citation Number: 9

Abstract

A facile synthesis of 4, 5-diamino-9-@-~-ribofuranosyl) pyolo [2, 3-d: 5, 4-d 'jdipyrimidin-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 Cthioxopyrimidin-2-one intermediate 3. A study involving the generality of this reagent for the annulation of cyclic o-aminonitriles ...