腈氧化物的研究(Ⅱ)--合成新诺明(SMZ)的新路线

高等学校化学学报 ›› 1987, Vol. 8 ›› Issue (2): 133.

腈氧化物的研究(Ⅱ)--合成新诺明(SMZ)的新路线

主序, 程铁明, 张玉芝, 贾琦, 蔡孟深

北京医科大学药学院

收稿日期:1985-10-20 出版日期:1987-02-24 发布日期:1987-02-24

Studies on Nitrile Oxide (Ⅱ)--A Novel Synthesis of Sinomin

Wang Xu, Cheng Tiemin, Zhang Yizhi, Jia Qi, Cai Mengshen

College of Pharmacy, Beijing Medical, University, Beijing

Received:1985-10-20 Online:1987-02-24 Published:1987-02-24

摘要/Abstract

摘要： 利用腈氧化物的1,3-偶极加成反应,合成新诺明(SMZ),以1,2,3-三氯代丁醛肟(Ⅰ_a),经转化为α,β-二氯代丁腈氧化物(Ⅱ_a)后,与对乙酰氨基苯磺酰胺加成,继而就地进行环合、消除反应,浮5-甲基-3-(对乙酰氨基苯磺酰氨基)异噁唑(Ⅲ_a),(Ⅲ_a)水解即得SMZ(Ⅳ_a)。同时依法制得5-苯基-3-(对氨基苯磺酰氨基)异噁唑(Ⅳ_b)。

Abstract: A novel synthesis of Sinomin by the 1,3-dipolar addition of nitrile oxide was reported. The 1,2,3-trichlorobutylaldehyde oxime (Ⅰα) was converted into 1,2-dichloropropylnitrile oxide (Ⅱα) on action of sodium methoxide. (Ⅱα) was treated with p-acetaminobenzenesulfamide, then the addition product was converted to 3-(p-acetaminobenzenesulfanilylamide-5-methylisoxazole(ASMZ) (Ⅲα) through cycli-zation and elimination in situ. The 3-(p-aminobenzenesulfanilylamido)-5-methyl-isoxazole(SMZ) (Ⅳα) was obtained when ASMZ was heated to 120℃ in 20% sodium hydroxide solution for 2 hr.In the same way the 3-(p-aminobenzenesulfanilylamido)-5-phenylisoxazolc (SPZ) (Ⅳb) was prepared.

TrendMD:

主序, 程铁明, 张玉芝, 贾琦, 蔡孟深. 腈氧化物的研究(Ⅱ)--合成新诺明(SMZ)的新路线. 高等学校化学学报, 1987, 8(2): 133.

Wang Xu, Cheng Tiemin, Zhang Yizhi, Jia Qi, Cai Mengshen . Studies on Nitrile Oxide (Ⅱ)--A Novel Synthesis of Sinomin. Chem. J. Chinese Universities, 1987, 8(2): 133.