Synthesis of 3-(3,4-Methylenedioxyphenyl)-5-Phenyl-2-Isoxazoline

化学工业与工程

Chemcial Industry and Engineering

2015, Vol. 32

Issue (1) :17-20 DOI: 10.13353/j.issn.1004.9533.2015.01.004

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Synthesis of 3-(3,4-Methylenedioxyphenyl)-5-Phenyl-2-Isoxazoline

Gong Yan, Tang Xiangyang, Qi Xin, Yan Chunli

Department of Chemistry, Tianjin University, Tianjin 300072, China

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Abstract In order to synthesize 3-(3,4-methylenedioxyphenyl)-5-phenyl-2-isoxazoline (3), a three-step synthetic procedure was developed, which involved condensation, chlorination and 1,3-dipolar cycloaddition. In the first two steps, the oxime (1) and hydroximoyl chloride (2) were synthesized from heliotropin. In the presence of triethylamine (Et₃N), a series of hydroximoyl chloride was transformed into nitrile oxide, followed by reacting with styrene via 1,3-dipolar cycloaddition to afford (3). Dosage of Et₃N and temperature of reaction were optimized. Under the optimized conditions, the yield of (3) is 92%.

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Keywords： 1,3-dipolar cycloaddition; oxime; hydroximoyl chloride; 3-(3,4-methylenedioxyphenyl)-5-pheny;l-2-isoxazoline

Received 2013-04-01;

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Gong Yan, Tang Xiangyang, Qi Xin, Yan Chunli.Synthesis of 3-(3,4-Methylenedioxyphenyl)-5-Phenyl-2-Isoxazoline[J] Chemcial Industry and Engineering, 2015,V32(1): 17-20

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