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    • 4. 发明授权
    • Synthesis of 1,3-oxathiolane sulfoxide compounds
    • 1,3-氧硫杂环戊烷亚砜化合物的合成
    • US5654441A
    • 1997-08-05
    • US528451
    • 1995-09-14
    • Derek James McPhee
    • Derek James McPhee
    • C07D327/04C07D327/06
    • C07D327/04C07D327/06
    • A process for the production of a 1,3-oxathiolane sulfoxide of the formula ##STR1## wherein X is an amino group of the formula --NHR, wherein R is hydrogen, phenyl, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, nitrophenyl, (C.sub.1 -C.sub.4 alkoxy)phenyl, furfuryl, halophenyl, tolyl, napthyl, biphenyl or hydroxyphenyl; or X is an alkoxy group of the formula --OR.sup.1 wherein R is C.sub.1 -C.sub.6 alkyl,which process comprises oxidizing a 1,3-oxathiolane of the formula ##STR2## wherein X is as defined above, in the presence of an effective amount of aqueous hydrogen peroxide and a sterically-hindered organoselenium compound of the formula ##STR3## wherein R.sup.2 is aryl, mono-, di- or tri-substituted with C.sub.1 -C.sub.3 alkyl,to the produce the 1,3-oxathiolane sulfoxide. This process stereoselectively produces the cis stereoisomer of the 1,3-oxathiolane sulfoxide. Additionally, there is disclosed a novel method for the preparation of 5,6-dihydro-2-methyl-1,4-oxathiin compounds using this process.
    • 制备式(I)的1,3-氧硫杂环戊烷亚砜的方法,其中X是式-NHR的氨基,其中R是氢,苯基,C 1 -C 8烷基,C 3 -C 6环烷基 ,硝基苯基,(C 1 -C 4烷氧基)苯基,糠基,卤代苯基,甲苯基,萘基,联苯基或羟基苯基; 或X是式-OR1的烷氧基,其中R是C 1 -C 6烷基,该方法包括在存在下述化合物的情况下,将式(XI)的1,3-氧硫杂环戊烷氧化为其中X如上定义: 有效量的过氧化氢水溶液和下式的影像有机硒化合物,其中R2是被C1-C3烷基单,二或三取代的芳基,以产生1,3-氧硫杂环戊烷亚砜。 该方法立体选择性地产生1,3-氧硫杂环戊烷亚砜的顺式立体异构体。 此外,公开了使用该方法制备5,6-二氢-2-甲基-1,4-氧硫杂化合物的新方法。