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US 6,855,831 B2Granted
Process for the preparation of cyclic diketones
AssigneeSyngenta Crop Protection AG
InventorsHermann Schneider, Christoph Lüthy, Andrew Edmunds
Life of this patent
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Abstract
The present invention relates to a process for the preparation of compounds of formula I: wherein the substituents are as defined in claim 1, by conversion of a compound of formula II: reaction of that compound with a compound of formula IV: X—C(O)—Q (IV), wherein X is a leaving group, to form a compound of formula V: and treatment of that compound in the presence of a base with catalytic amounts of cyanide ions.
Claims1
A process for the preparation of a compound of formula I:
- wherein Q is a mono- or poly-substituted phenyl, pyridyl or heteroaryl group so selected that the compound of formula I has a pK value of from 1 to 5;
- D is hydrogen or R3;
- E is hydrogen or R4;
- A is C1-C2alkylene, which may be mono- or poly-substituted by R5;
- R1, R2, R3, R4 and R5 are each independently of the others hydrogen, C1-C4alkyl, phenyl, C1-C4alkoxy, halogen, hydroxy, cyano, hydroxycarbonyl or C1-C4alkoxycarbonyl;
- which comprises
- a) converting a compound of formula II:
- wherein R1, R2, A, D and E are as defined for formula I, either in the presence of an amine base and a catalytic amount of a cyanide or in the presence of an alkali metal alcoholate or alkaline earth metal alcoholate, to a salt of formula III:
- wherein R1, R2, A, D and E are as defined for formula I and M+ is an alkali metal ion, alkaline earth metal ion or ammonium ion,
- b) reacting that compound with a compound of formula IV:
- X—C(O)—Q (IV),
- wherein X is a leaving group and Q is as defined for formula I, to yield a compound of formula V:
- wherein R1, R2, A, D, E and Q are as defined for formula I, and
- c) converting that compound in the presence of catalytic amounts of cyanide ions and in the presence of a base to a compound of formula I.
11 more elements
Dependencies are inferred from the claim text.