叔丁醇钾促进的对甲苯磺酰基氮杂环丙烷与取代炔丙醇反应研究  

Studies on the Reaction Between N-Ts Aziridines and Substituted Propargyl Alcohol Promoted by t-BuOK

作　　者：刘启宾 Liu Qibin(Dalian Allychem Company Limited,Dalian,Liaoning 116620,China)

机构地区：[1]大连联化化学有限公司,辽宁大连116620

出　　处：《化学世界》2021年第2期105-111,共7页Chemical World

摘　　要：以叔丁醇钾作为促进剂,采用正丁基、氢基、芳基取代的炔丙醇(2),与(S)-型或消旋对甲苯磺酰基氮杂环丙烷(1)分别发生开环、开环/异构化、开环/异构化/关环,从而得到不同的产物(2-炔-1-基氧代-2-基-4-甲基苯磺酰胺衍生物3、丙-1,2-二烯氧-2-基-4-甲基苯磺酰胺衍生物4或4-对甲苯磺酰基-1,4-噁嗪衍生物5)。采用强吸电子和强供电子芳基炔丙醇进行对比试验,发现强吸电子芳基相比强供电子芳基更易发生开环/异构化/关环反应,生成1,4-噁嗪。Using t-BuOK as an effective promoting reagent, n-butyl-, hydrogen-and aryl-substituted propargyl alcohols(2) reacted with(S)-or racemic N-Ts aziridines(1) to afford different products [2-(prop-2-yn-1-yloxy)-4-methylbenzene sulfonamide derivatives(3), 2-(propa-1,2-dien-1-yloxy)ethyl)-4-methylbenzenesulfonamide derivatives(4) or 4-tosyl-1,4-oxazine derivatives(5)] through ring opening, ring opening/isomerization and ring opening/isomerization/ring closing, respectively. Compared to the electron-withdrawing and electron-donating aryl propargyl alcohol, it was found that the strong electron-withdrawing aryl group is easier to afford 1,4-oxazine derivatives through ring opening/isomerization/ring closing reaction than the strong electron-donating aryl group.

关 键 词：叔丁醇钾 炔丙醇 对甲苯磺酰基氮杂环丙烷 1 4-噁嗪 开环/异构化/关环 

分 类 号：O621.3[理学—有机化学]