Conjugated triene compound, and preparation and application thereof
AssigneeOriental (Luzhou) Agrochemicals. Co., Ltd.
InventorsBangchi Chen, Yinwei Sun, Zhongyuan Wang, Teng Lai
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Abstract
Disclosed are a type of conjugated triene compounds (1), and a preparation and application thereof. In this method, a 2-(cyclohexenylidene)malonic acid derivative is sequentially subjected to isomerization, halogenation reaction in the presence of a halogenating agent and dehydrohalogenation to prepare the conjugated triene compounds (1). This disclosure further provides a method of preparing a 2-aryl malonic acid derivative from the conjugated triene compounds (1) through aromatization reaction.
Claims12
A conjugated triene 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;
- and
- X1 and X2 each are independently a cyano group or —COR6 where 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.
A method for preparing a conjugated triene compound of formula (1), comprising:
- subjecting compound (2) to isomerization to produce compound (3);
- and
- subjecting the compound (3) to halogenation in the presence of a halogenating agent and dehydrohalogenation to produce the conjugated triene compound of formula (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;
- and
- X1 and X2 each are independently a cyano group or —COR6 where 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-C2 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur.
A method of preparing a 2-aryl malonic acid derivative of formula (4), comprising:
- aromatizing compound (1) to produce the 2-aryl malonic acid derivative (4), 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 or sulfur;
- and
- X1 and X2 each are independently a cyano group or —COR6 where 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-C2 aryl) amino group, a di(C6-C2 aryl) amino group, a C6-C2 aryl group or a heteroaryl group containing one or two atoms selected from nitrogen, oxygen and sulfur.
A method of synthesizing 2,2-dimethyl-,8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl ester, comprising:
- aromatizing 2-(2,6-diethyl-4-methyl-3-ene-1-cyclohexylidene)malononitrile sequentially 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 2,2-dimethyl-,8-(2,6-diethyl-4-methylphenyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl ester, as shown in the following reaction scheme:
Dependencies are inferred from the claim text.