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    • 24. 发明申请
    • PROCESS FOR THE PREPARATION OF SUBSTITUTED 5-HYDROXY-OXAZOLIDIN-4-ONE
    • 制备取代的5-羟基 - 恶唑烷-4-酮的方法
    • WO1996037483A1
    • 1996-11-28
    • PCT/GB1996001149
    • 1996-05-13
    • ZENECA LIMITEDCOX, John, MichaelPEARSON, David, Philip, JohnKOZAKIEWICZ, Anthony, MarianMOORE, Richard, ButlerMITCHELL, GlynnLANGTON, David, WilliamELLIS, Russel, Martin
    • ZENECA LIMITED
    • C07D263/18
    • C07D263/18C07D263/28
    • A process for the synthesis of a compound of general formula (II), wherein: R and R are each independently hydrogen or C1-C4 alkyl; A is an aromatic or heteroaromatic ring system optionally substituted with one or more substituents selected from: halogen or C1-C10 hydrocarbyl, -O(C1-C10 hydrocarbyl), -S(C1-C10 hydrocarbyl), -SO(C1-C10 hydrocarbyl) or -SO2(C1-C10 hydrocarbyl), cyano, nitro, SCN, SiR 3 (where each R is independently C1-C4 alkyl or phenyl), COR , CR NOR , NHOH, ONR R , SF5, COOR , SO2NR R , OR or NR R ; and in which any ring nitrogen atom may be quaternised or oxidised; alternatively, any two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring in which any carbon or quaternised nitrogen atom may be substituted with any of the groups mentioned above for A or in which a ring carbon atom may be oxidised; R and R are each independently hydrogen or C1-C10 hydrocarbyl; R is hydrogen, C1-C10 hydrocarbyl, SO2(C1-C10 hydrocarbyl), CHO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR R ; R and R are each independently hydrogen, C1-C10 hydrocarbyl, O(C1-C10 hydrocarbyl), SO2(C1-C10 hydrocarbyl), CHO, CO(C1-C10 hydrocarbyl), COO(C1-C10 hydrocarbyl) or CONR R ; any of the hydrocarbyl groups within the group A may optionally be substituted with halogen (i.e. chlorine, bromine, fluorine or iodine), hydroxy, SO2NR R (where R and R are independently H or C1-C6 alkyl), cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 alkylsulphinyl, C1-C6 alkylsulphonyl, carboxy, carboxyamide, in which the groups attached to the N atom may be hydrogen or lower hydrocarbyl optionally substituted with halogen; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such as phenyl; the process comprising cyclising a compound of general formula (VII); wherein A, R and R are as defined for general formula (II), R is hydrogen, benzyl or benzyl substituted with up to five substituents selected from halo, C1-C6 alkyl, O(C1-C6 alkyl) or nitro and R is C1-C8 alkyl, benzyl or benzyl substituted with up to five of the substituents mentioned above for R .
    • 一种合成通式(II)化合物的方法,其中:R 2和R 3各自独立地为氢或C 1 -C 4烷基; A是任选被一个或多个选自以下的取代基取代的芳族或杂芳族环系:卤素或C 1 -C 10烃基,-O(C 1 -C 10烃基),-S(C 1 -C 10烃基), - (C 1 -C 10烃基 )或-SO 2(C 1 -C 10烃基),氰基,硝基,SCN,SiR c 3(其中每个R c独立地为C 1 -C 4烷基或苯基),COR 7, 8,NHOH,ONR 7 R 8,SF 5,COOR 7,SO 2 NR 7 R 8,OR 9或NR 10 R 11; 并且其中任何环氮原子可被季铵化或氧化; 可选地,基团A的任何两个取代基可以结合形成稠合的5或6元饱和或部分饱和的碳环或杂环,其中任何碳或季铵化的氮原子可被上述任何A或 其中环碳原子可被氧化; R 7和R 8各自独立地为氢或C 1 -C 10烃基; R 9是氢,C 1 -C 10烃基,SO 2(C 1 -C 10烃基),CHO,CO(C 1 -C 10烃基),COO(C 1 -C 10烃基)或CONR 7 R 8; R 10和R 11各自独立地为氢,C 1 -C 10烃基,O(C 1 -C 10烃基),SO 2(C 1 -C 10烃基),CHO,CO(C 1 -C 10烃基) 烃基)或CONR 7 R 8; 基团A中的任何烃基可以任选地被卤素(即氯,溴,氟或碘),羟基,SO 2 NR a R b(其中R a和R b独立地是H 或C 1 -C 6烷基),氰基,硝基,氨基,一烷基氨基和二烷基氨基,其中烷基具有1至6个或更多个碳原子,酰基氨基,C 1 -C 6烷氧基,C 1 -C 6卤代烷氧基,C 1 -C 6烷硫基,C 1 -C 6烷基亚磺酰基,C 1 -C 6烷基磺酰基,羧基,羧酰胺,其中与N原子连接的基团可以是氢或任选被卤素取代的低级烃基; 烷氧基羰基,其中烷氧基可以具有1至6个或更多个碳原子,或芳基如苯基; 该方法包括环化通式(VII)的化合物; 其中A,R 2和R 3如通式(II)所定义,R 20是氢,被至多5个选自卤素,C 1 -C 6烷基,O(C 1 -C 6) -C 1-6烷基)或硝基,R 21是C 1 -C 8烷基,被至多五个上述R 20取代基取代的苄基或苄基。