公开(公告)号：WO1995033719A1

公开(公告)日：1995-12-14

申请号：PCT/GB1995001224

申请日：1995-05-26

Applicant: ZENECA LIMITED ,  COX, John, Michael ,  CLOUGH, John, Martin ,  BARNES, Nigel, John ,  PEARSON, David, Philip, John ,  MATTHEWS, Ian, Richard ,  VOHRA, Shaheen, Khatoon ,  SMITH, Stephen, Christopher ,  MITCHELL, Glynn ,  BARBER, Richard, Anthony ,  ELLIS, Russell, Martin ,  LANGTON, David, William ,  GILLEN, Kevin, James ,  HATTER, Glenn ,  KOZAKIEWICZ, Anthony, Marian ,  BACON, David, Philip ,  BELLINI, Peter

Inventor： ZENECA LIMITED

IPC: C07D207/26

CPC classification number: C07D207/26 ,  A01N43/36 ,  A01N43/40 ,  A01N43/50 ,  A01N43/54 ,  A01N43/76 ,  A01N43/78 ,  A01N43/80 ,  A01N47/06 ,  A01N47/18 ,  A01N47/24 ,  A01N47/36 ,  A01N51/00 ,  A01N55/00 ,  C07C271/10 ,  C07C271/32 ,  C07C271/40 ,  C07D207/273 ,  C07D263/18 ,  C07D277/14 ,  C07D277/16 ,  C07D277/18 ,  C07D401/04 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C07D413/04 ,  C07D417/04

Abstract: Compounds of general formula (I), wherein X is O, S or CR R ; each R and R is, independently, hydrogen or C1-C4 alkyl; Z is O, S or NR ; n is 0 or 1; Y is O, S, NR or CR R ; R is H, OH, CHO, NR R or C1-C10 hydrocarbyl, 0-(C1-C10 hydrocarbyl), either of which may be substituted with one orm ore substituents chosen from OR , COR , COOR , OCOR , CN, halogen, S(O)pR , NR R , NO2, NR COR , NR CONR R , CONR R or heterocyclyl; R , R and R are each, independently, hydrogen, C1-C6 hydrocarbyl or C1-C6 halohydrocarbyl; p is 0, 1 or 2; alternatively: when Y is NR or CR R , and: a) Z is NR ; or b) n is 0; the substituents of Y and Z or Y and R may together form a bridge represented by the formula -Q -Q - or -Q -Q -Q -, where Q , Q and Q each independently represent CR R , =CR , CO, NR , =N, O or S; each or R and R independently represents hydrogen, C1-C4 alkyl, OH or halogen; R represents hydrogen or C1-C4 alkyl; W is O or S; R is hydrogen or C1-C10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms; R and R are each independently hydrogen or C1-C4 alkyl; A is an aromatic or heteroaromatic ring system optionally substituted alternatively, two or more 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 part of a carbonyl group or a nitrogen atom may be oxidised.

Abstract translation: 通式（I）的化合物，其中X是O，S或CR 4 R 5; 每个R 4和R 5独立地是氢或C 1 -C 4烷基; Z是O，S或NR 4; n为0或1; Y是O，S，NR 6或CR 4 R 5; R 6是H，OH，CHO，NR 16 R 17或C 1 -C 10烃基，O-（C 1 -C 10烃基），其中任一个可以被一个选自OR 16的取代基取代 ，COR 16，OCOR 16，CN，卤素，S（O）p R 16，NR 16 R 17，NO 2，NR 16 COR 17， NR 16 CONR 17 R 18，CONR 16 R 17或杂环基; R 16，R 17和R 18各自独立地为氢，C 1 -C 6烃基或C 1 -C 6卤代烃基; p为0,1或2; 或者：当Y是NR 6或CR 4 R 5时，和：a）Z是NR 4; 或b）n为0; Y和Z或Y和R 1的取代基可以一起形成由式-Q 1 -Q 2 - 或-Q 1 -Q 2 -Q 3 - 其中Q 1，Q 2和Q 3各自独立地表示CR 12 R 13，= CR 12，CO，NR 14，= N，O或S; 每个或R 12和R 13独立地表示氢，C 1 -C 4烷基，OH或卤素; R 14表示氢或C 1 -C 4烷基; W为O或S; R 1是氢或C 1 -C 10烃基或具有3至8个环原子的杂环基; R 2和R 3各自独立地为氢或C 1 -C 4烷基; A是任选地任选取代的芳族或杂芳族环系统，组A中的两个或多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氮原子可以是 被上述任何A取代或环碳原子可以是羰基或氮原子的一部分被氧化。

公开(公告)号：WO1997028138A1

公开(公告)日：1997-08-07

申请号：PCT/GB1997000130

申请日：1997-01-17

Applicant: ZENECA LIMITED ,  COX, John, Michael ,  MITCHELL, Glynn ,  VOHRA, Shaheen, Khatoon

Inventor： ZENECA LIMITED

IPC: C07D263/18

CPC classification number: C07D277/14 ,  C07D263/18

Abstract: The present invention relates to a process for the production of a hydroxyoxazolidinone of formula (I) wherein A represents optionally substituted phenyl; which process comprises the step of treating a hydroxythiazolidinone of formula (II) in which A is as defined for formula (I); with an oxidising agent. The compounds of formula (I) may be used as intermediates in the synthesis of herbicidally active compounds.

Abstract translation: 本发明涉及制备式（I）的羟基恶唑烷酮的方法，其中A表示任意取代的苯基; 该方法包括处理其中A如式（I）所定义的式（II）的羟基噻唑烷酮的步骤; 与氧化剂。 式（I）化合物可用作合成除草活性化合物的中间体。

公开(公告)号：WO1996037466A1

公开(公告)日：1996-11-28

申请号：PCT/GB1996001150

申请日：1996-05-13

Applicant: ZENECA LIMITED ,  COX, John, Michael ,  GILLEN, Kevin, James ,  ELLIS, Russell, Martin ,  VOHRA, Shaheen, Khatoon ,  SMITH, Stephen, Christopher ,  MATTHEWS, Ian, Richard

Inventor： ZENECA LIMITED

IPC: C07D207/273

CPC classification number: C07D207/273

Abstract: A process for the preparation of a compound of general formula (II) wherein R is hydrogen or C1-C10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms, either of which 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), SiR 3 (where each R is independently C1-C4 alkyl or phenyl), 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 optionally substituted lower hydrocarbyl; alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, or aryl such as phenyl; each R , R , R and R is 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; R is hydrogen, halogen OH3 or OCONHR , wherein R is as defined above; the process comprising cyclising a compound of general formula (III), wherein A, R , R , R , R and R are as defined in general formula (II) and R is a leaving group such as a halogen atom; under basic conditions.

Abstract translation: 制备通式（II）的化合物的方法，其中R 1是氢或具有3至8个环原子的C 1 -C 10烃基或杂环基，其任一个可以任选地被卤素（即氯，溴， 氟或碘），羟基，SO 2 NR a R b（其中R a和R b独立地为H或C 1 -C 6烷基），SiR c 3（其中每个R c独立地为 C 1 -C 6烷基或苯基），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; 每个R 2，R 3，R 4和R 5独立地是氢或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; 基团A的任何两个取代基可以组合形成稠合的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以被上述任何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），COO 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; R 21是氢，卤素OH 3或OCONHR 1，其中R 1如上定义; 该方法包括使通式（III）的化合物环化，其中A，R 2，R 3，R 4，R 5和R 21如通式（II）中所定义，和 R 25为离去基团，例如卤素原子; 在基本条件下

公开(公告)号：WO1997019920A1

公开(公告)日：1997-06-05

申请号：PCT/GB1996002809

申请日：1996-11-15

Applicant: ZENECA LIMITED ,  MITCHELL, Glynn ,  VOHRA, Shaheen, Khatoon

Inventor： ZENECA LIMITED

IPC: C07D207/26

CPC classification number: C07D207/273

Abstract: A process for preparing a compound of formula (IIa) or (IIb) wherein R , R , R and R independently represent hydrogen or C1-C4 alkyl; and A is an optionally substituted aromatic or heteroaromatic ring system; the process comprising the steps of: (a) reacting a racemic mixture of a compound of formula (II), wherein R , R , R , R and A are as defined for formulae (IIa) and (IIb); with a sterically hindered chiral esterifying agent to form enantiomers of formulae (IIIa) and (IIIb) wherein R , R , R , and R and A are as defined for formulae (IIa) and (IIb) and R is a chiral sterically hindered residue; (b) separating the diastereoisomers of formulae (IIIa) and (IIIb); and (c) converting the diastereoisomers of formulae (IIIa) and (IIIb) separately to compounds of formulae (IIa) and (IIb) respectively by acid or base hydrolysis. If required, the unwanted enantiomer of formula (IIa) or (IIb) may be inverted to give the preferred isomer.

Abstract translation: 制备式（IIa）或（IIb）化合物的方法，其中R 2，R 3，R 4和R 5独立地表示氢或C 1 -C 4烷基; 并且A是任选取代的芳族或杂芳族环系; 该方法包括以下步骤：（a）将式（II）化合物的外消旋混合物与式（II）化合物反应，其中R 2，R 3，R 4，R 5和A如式 （IIa）和（IIb）; 与空间位阻手性酯化剂反应以形成式（IIIa）和（IIIb）的对映异构体，其中R 2，R 3，R 4和R 5和A如式（IIa）所定义， 和（IIb）和R 15是手性空间位阻残基; （b）分离式（IIIa）和（IIIb）的非对映异构体; 和（c）通过酸或碱水解分别将式（IIIa）和（IIIb）的非对映异构体分别转化为式（IIa）和（IIb）化合物。 如果需要，可以将式（IIa）或（IIb）的不需要的对映异构体倒置，得到优选的异构体。