Halogenated conjugated diene compound, and preparation and application thereof
AssigneeOriental (Luzhou) Agrochemicals. Co., Ltd.
InventorsBangchi Chen, Yinwei Sun, Zhongyuan Wang, Miao Lin
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Abstract
Disclosed are a type of halogenated conjugated diene compounds (1), and preparation and application thereof. In this method, a conjugated diene compounds is subjected to halogenation reaction to prepare the compound (1). This disclosure further provides a method of preparing a 2-arylmalonic acid derivative from the compound (1) through dehydrohalogenation and aromatization reaction.
Claims10
A halogenated conjugated diene compound of formula (1),
- wherein:
- R1, R2, R3, R4 and R5 each are 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 each are independently a cyano group or —COR6, where the R6 is hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a C1-C10 alkylamino group, a C6-C12 arylamino group, a di(C1-C10 alkyl) amino group, a (C1-C10 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;
- and
- X is halogen.
A method for preparing a halogenated conjugated diene compound of formula (1), comprising:
- subjecting compound (2) to halogenation in the presence of a halogenating agent to obtain the halogenated conjugated diene compound (1), as shown in the following reaction scheme:
- wherein:
- R1, R2, R3, R4 and R5 each are 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 each are independently a cyano group or —COR6, where the R6 is hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a C1-C10 alkylamino group, a C6-C12 arylamino group, a di(C1-C10 alkyl) amino group, a (C1-C10 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;
- and
- X is halogen.
A method of preparing a 2-aryl malonic acid derivative of formula (3), comprising:
- subjecting compound (1) to dehydrohalogenation and aromatization reactions to obtain the 2-aryl malonic acid derivative (3), as shown in the following reaction scheme:
- wherein:
- R1, R2, R3, R4 and R5 each are 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 each are independently a cyano group or —COR6, where the R6 is hydrogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a C6-C12 aryloxy group, an amino group, a C1-C10 alkylamino group, a C6-C12 arylamino group, a di(C1-C10 alkyl) amino group, a (C1-C10 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;
- and
- X is halogen.
A method of synthesizing [8-(2,6-diethyl-4-methylphenyl)-7-oxo-1,2,4,5-tetrahydro-7H-pyrazolo[1,2-d][1,4,5]o xadiazepin-9-yl]2,2-dimethylpropanoate, comprising:
- subjecting 2-(3-chloro-6-ethyl-2-ethylidene-4-methyl-1-cyclohexylidene)malononitrile to dehydrohalogenation and aromatization reactions in the presence of a catalyst to obtain 2-(2,6-diethyl-4-methylphenyl) malononitrile;
- reacting the 2-(2,6-diethyl-4-methylphenyl) malononitrile 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]o xadiazepin-9-yl]2,2-dimethylpropanoate, as shown in the following reaction scheme:
- wherein the catalyst is selected from the group consisting of an alkali metal halide, an alkaline earth metal halide and a mixture thereof.
Dependencies are inferred from the claim text.