Method for preparing 2-arylmalonic acid derivative and intermediate, and use thereof
AssigneeOriental (Luzhou) Agrochemicals. Co., Ltd.
InventorsBangchi CHEN, Yinwei SUN, Zhongyuan WANG, Tao JIN
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Abstract
Disclosed herein is a method for preparing a 2-arylmalonic acid derivative. In this method, a cyclohexadiene compound is used as a raw material, and sequentially undergoes an isomerization reaction, a halogenation reaction in the presence of a halogenating agent and a dehydrohalogenation-aromatization reaction to obtain a 2-arylmalonic acid derivative (3). An intermediate for preparing the 2-arylmalonic acid derivative (3) and use of the intermediate are also disclosed.
Claims10
A method for preparing a 2-arylmalonic acid derivative of formula (3), comprising:
- (1) subjecting a compound (1) to an isomerization reaction to obtain an intermediate (2), as shown in the following reaction scheme:
- and
- (2) subjecting the intermediate (2) to a halogenation reaction in the presence of a halogenating agent and a dehydrohalogenation-aromatization reaction to obtain the 2-arylmalonic acid derivative (3), as shown in the following reaction scheme:
- wherein R1, R2, R3, R4 and R5 are each independently hydrogen, a C1-C10 alkyl group, a C6-C12 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur;
- Y1 and Y2 are each independently cyano or —COR6where R6 is hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, amino, a C1-C10 alkylamino group, a C6-C12 arylamino group, a di-(C1-C10 alkyl)-amino group, a alkyl)-(C6-C12 aryl)-amino group, a di-(C6-C12 aryl) amino group, a C6-C12 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur.
A compound of formula (2),
- wherein:
- R1, R2, R3, R4 and R5 are each independently hydrogen, a C1-C10 alkyl group, a C6-C12 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur;
- Y1 and Y2 are each independently cyano or —COR6 where R6 is hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, amino, a C1-C10 alkylamino group, a C6-C12 arylamino group, a di-(C1-C10 alkyl)-amino group, a alkyl)-(C6-C12 aryl)-amino group, a di-(C6-C12 aryl) amino group, a C6-C12 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur.
A method for preparing [8-(2,6-diethyl-4-methylphenyl)-7-oxo- 1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl]2,2-dimethylpropanoate, comprising:
- subjecting 2-(2,6-diethyl-4-methylphenyl)malononitrile to reaction in the presence of concentrated sulfuric acid to obtain 2-(2,6-diethyl-4-methylphenyl)malonamide;
- and
- subjecting the 2-(2,6-diethyl-4-methylphenyl)malonamide, [1,4,5]-oxadiazepine dihydrochloride and pivaloyl chloride to reaction in the presence of triethylamine to obtain
- [8-(2,6-diethyl-4-methylphenyl)-7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl]2,2-dimethylpropanoate, as shown in the following reaction scheme:
Dependencies are inferred from the claim text.