Bi Xihe, Dong Dewen, Li Yan, Liu Qun, Zhang Qian
Department of Chemistry, Northeast Normal University, Changchun 130024, PR China.
J Org Chem. 2005 Dec 23;70(26):10886-9. doi: 10.1021/jo052032g.
[reaction: see text] 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 alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na2S x 9H2O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 5l, an inhibitor of DNA-dependent protein kinase (DNA-PK).
[反应：见正文] 通过易得的α-烯丙酰基乙烯酮-(S,S)-缩醛1与九水合硫化钠（Na₂S·9H₂O）进行形式上的[5C + 1S]环化反应，已开发出一种简便高效的合成高度取代的2,3-二氢噻喃-4-酮2的路线，并将其用于合成2-(4-氯苯基)-6-(吗啉-4-基)-4H-噻喃-4-酮5l，一种DNA依赖性蛋白激酶（DNA-PK）的抑制剂。
