Synthesis of Octahydropyrano[2,3-d]Pyrimidine Derivatives via Tetrahydropyrano[3,2-e][1,3]Thiazolo[3,2-a]Pyrimidine and 2,6-Dichlorobenzonitrile Oxide

Abstract

N1-substituted octahydro-1 H-pyrano[2,3- d]pyrimidines derivatives were prepared in moderate yield by the reaction of methyl [(4a RS,5 SR,10a RS)-5-aryl-2-oxo-3,4,4 a,10 a-tetrahydro-2 H,5 H-pyrano[3,2- e][1,3]thiazolo[3,2- a]pyrimidin-8(9 H)-ylidene]acetate and 2,6-dichorobenzonitrile oxide via a domino 1,3-dipolar cycloaddition/ring-opening/dethionation process. The structures of the products were characterised by spectroscopic and X-ray crystallographic analysis.