[5C+ 1S] annulation: A facile and efficient synthetic route toward functionalized 2, 3-dihydrothiopyran-4-ones

X Bi, D Dong, Y Li, Q Liu, Q Zhang

Index: Bi, Xihe; Dong, Dewen; Liu, Qun; Pan, Wei; Zhao, Lei; Li, Bing Journal of the American Chemical Society, 2005 , vol. 127, # 13 p. 4578 - 4579

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Citation Number: 65

Abstract

A facile and efficient synthetic route toward highly substituted 2, 3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C+ 1S] annulation of readily available α-alkenoyl ketene- (S, S)-acetals 1 with sodium sulfide nonahydrated salt (Na2S⊙ 9H2O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4 H-thiopyran-4-one 5l, an inhibitor of DNA-dependent protein kinase (DNA-PK).