5-甲基-3-喹喔啉-2-基-4-乙氧羰基异噁唑及其衍生物的合成  

Synthesis of Ethyl 5-Methyl-3-(quinoxalin-2-yl)-isoxazole-4 Carboxylate and Their Derivatives

作　　者：王厚勇[1] 刘方明[1,2] 阎琴[1] 郭群胜[3] 

机构地区：[1]新疆大学化学化工学院 [2]杭州师范学院化学系杭州310012 [3]南开大学元素有机化学研究所

出　　处：《有机化学》2005年第1期75-80,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos. 29702007; 20162004)资助项目.

摘　　要：以 α-氯代喹喔啉-2-甲醛肟(3)与乙酰乙酸乙酯的钠盐经 1,3-偶极环加成制得关键中间体 5-甲基-3-喹喔啉-2-基-4-乙氧羰基异噁唑(4). 以化合物4为原料在不同条件下, 合成了一系列新的1,3,4-噁二唑啉(7), 1,2,4-均三唑的Mannich碱衍生物 10a～10f, 11a～11f, 12a～12f. 化合物的结构经元素分析, IR, H NMR 和 MS确认, 并对其波谱性质进行了讨论.The key intermediate ethyl 5-methyl-3-(quinoxalin-2-yl)-isoxazole-4-carboxylate (4) was ob- tained by 1,3-dipolar cycloaddition reaction of 2-(1-hydroxylimino-1-chloro-methyl)-quinoxaline (3) with sodium 1-aceto-1-ethoxycarbonyl-methide, which was converted to hydrazide 5 by treating with hydrazine hydrate. Condensation of 5 with aromatic aldehydes gave corresponding hydrazones 6, then cyclization of 6 in Ac2O afforded 1,3,4-oxadiazolines 7a～7f. Thiosemicarbazides 8 prepared by treatment of the hydrazide 5 with suitable isothiocyanates, were cyclized in 1 mol?L-1 NaOH aqueous solution to give 5-thio-1,2,4- triazolines 9, and the Mannich base 10a～10f, 11a～11f and 12a～12f were synthesized. Their structures were analyzed and established by elemental analysis, IR, H NMR and MS spectra. 1

关 键 词：甲基 噁唑 氯代 羰基 合成 衍生物 乙酰乙酸乙酯 环加成 波谱性质 三唑 

分 类 号：O626[理学—有机化学] TQ225[理学—化学]