Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-07-28
2000-02-08
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548226, 548110, C07D26304, C07D23104
Patent
active
060229764
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the production of hydroxy-substituted oxazolidinones, particularly 5-hydroxyoxazolidinones which are useful as intermediates in the synthesis of herbicidally active compounds.
Oxazolidinone compounds which are active as herbicides are known from WO 94/13652 and WO 95/33719 (published after the priority date of the present application). These documents disclose inter alia compounds of the formula: ##STR1##
wherein Z is O, S or NR.sup.4 ;
W is O or S;
R.sup.1 is hydrogen, or C.sub.1 -C.sub.10 hydrocarbyl or heterocyclyl having 3 to 8 ring atoms either of which may optionally be substituted with halogen, hydroxy, SO.sub.2 NR.sup.a R.sup.b (where R.sup.a and R.sup.b independently represent hydrogen or C.sub.1 -C.sub.6 alkyl), SiR.sup.c.sub.3 (where each R.sup.c is independently C.sub.1 -C.sub.4 alyl or phenyl), cyano, nitro, amino, mono- and di-C.sub.1 -C.sub.6 alkylamino, acylamino, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 haloalkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkylsufinyl, C.sub.1 -C.sub.6 alylsulfonyl, carboxy, carboxyamide (in which the groups attached to the N atom may be hydrogen or optionally substituted C.sub.1 -C.sub.10 hydrocarbyl), C.sub.1 -C.sub.6 alkoxycarbonyl or aryl;
R.sup.2, R.sup.3 and R.sup.4 independently represent hydrogen or C.sub.1 -C.sub.4 alkyl;
n is 0 or 1;
Y is O, S or NR.sup.5 ;
R.sup.5 is hydrogen, hydroxy, CHO or NR.sup.6 R.sup.7, or C.sub.1 -C.sub.10 hydrocarbyl or O(C.sub.1 -C.sub.10 hydrocarbyl) either of which may be substituted with up to two substituents selected from OR.sup.6, COR.sup.6, COOR.sup.6, OCOR.sup.6, cyano, halogen, S(O).sub.p R.sup.6, NR.sup.6 R.sup.7, nitro, NR.sup.6 COR.sup.7, NR.sup.6 CONR.sup.7 R.sup.8, CONR.sup.6 R.sup.7 and heterocyclyl;
R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen or C.sub.1 -C.sub.6 hydrocarbyl optionally substituted with one or more halogen atoms;
p is 0, 1 or 2;
alternatively, when Y is NR.sup.5 and either Z is NR.sup.4 or n is 0, R.sup.5 and R.sup.4 or R.sup.1 may together form a bridge represented by the formula --Q.sup.1 --Q.sup.2 -- or --Q.sup.1 --Q.sup.2 --Q.sup.3 --, where Q.sup.1, Q.sup.2 and Q.sup.3 independently represent CR.sup.9 R.sup.10, .dbd.CR.sup.9, CO, NR.sup.11, .dbd.N, O or S;
R.sup.9 and R.sup.10 independently represent hydrogen, C.sub.1 -C.sub.4 alky, hydroxy or halogen;
R.sup.11 represents hydrogen or C.sub.1 -C.sub.4 alkyl;
A is an aromatic or heteroaromatic ring system optionally substituted with one or more substituents selected from halogen, C.sub.1 -C.sub.10 hydrocarbyl, S(O).sub.p (C.sub.1 -C.sub.10 hydrocarbyl), cyano, nitro, SCN, SiR.sup.c.sub.3 (where each R.sup.c is independently C.sub.1 -C.sub.4 alkyl or phenyl), COR.sup.12, CR.sup.12 NOR.sup.13, NHOH, ONR.sup.12 R.sup.13, SF.sub.5, COOR.sup.12, SO.sub.2 NR.sup.12 R.sup.13, OR.sup.14 and NR.sup.15 R.sup.16 ; 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 as substituents on A, a ring carbon atom may form part of a carbonyl group or a nitrogen atom may be oxidised;
R.sup.12 and R.sup.13 independently represent hydrogen or C.sub.1 -C.sub.10 hydrocarbyl;
R.sup.14 is hydrogen, C.sub.1 -C.sub.10 hydrocarbyl, SO.sub.2 (C.sub.1 -C.sub.10 hydrocarbyl), CHO, CO(C.sub.1 -C.sub.10 hydrocarbyl), COO(C.sub.1 -C.sub.10 hydrocarbyl) or CONR.sup.12 R.sup.13 ;
R.sup.15 and R.sup.16 independently represent hydrogen, C.sub.1 -C.sub.10 hydrocarbyl, O(C.sub.1 -C.sub.10 hydrocarbyl), SO.sub.2 (C.sub.1 -C.sub.10 hydrocarbyl), CHO, CO(C.sub.1 -C.sub.10 hydrocarbyl), COO(C.sub.1 -C.sub.10 hydrocarbyl) or CONR.sup.12 R.sup.13 ; and
any of the hydrocarbyl groups within the group A, whether the hydrocarbyl group is a group on its own or part of a larger group, may optionally be substituted with halogen, hydroxy, SO.sub.2
REFERENCES:
patent: 5856273 (1999-01-01), Kay et al.
Cox John Michael
Mitchell Glynn
Vohra Shaheen Khatoon
Keating Dominic
Richter Johann
Thomson Marian T.
Zeneca Limited
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