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一种有效合成5-氟烷基噁唑啉的方法
  • ISSN号：0253-2786
  • 期刊名称：有机化学
  • 时间：2013.8.15
  • 页码：1782-1790
  • 分类：O625.322[理学—有机化学;理学—化学]
  • 作者机构：[1]华东理工大学化学与分子工程学院,上海200237, [2]上海应用技术学院化学与环境工程学院,上海201418
  • 相关基金：国家自然科学基金（Nos.20972050,21172148）资助项目.
  • 相关项目：新型氟代HMG-CoA还原酶抑制剂的设计与合成
作者： 杨波|方向|杨雪艳|吴范宏|
关键词： 噁唑啉, 氟烷基化, O-环合, 自由基反应, oxazoline, fluorinated alkyl, O-cyclization, free radical reaction
中文摘要：

报道了一种有效地合成5-氟烷基噁唑啉的方法．异氰酸酯与烯丙基胺在二氯甲烷中室温反应得到1-烯丙基-3-芳基脲．1-烯丙基-3-芳基脲与氟烷基碘在乙腈和水的混合液中由连二亚硫酸钠引发在室温下发生自由基加成反应得到氟烷基化的加成产物．加成产物在水或N,N-二甲基甲酰胺（DMF）中加热回流反应得到5-氟烷基噁唑啉．同时我们也可以通过由偶氮二异丁腈（AIBN）引发的1-烯丙基-3-芳基脲的加成环合反应得到5-氟烷基噁唑啉．

英文摘要：

An efficient and convenient protocol for the synthesis of 5-fluoroalkyl-2-oxazoline is described. The 1-allyl-3-arylurea was synthesized by the reaction of isocyanate with ally1 amine in methylene chloride at room temperature. The reaction of 1-allyl-3-arylurea with fluoroalky iodide initiated by sodium dithionite in aqueous acetonitrile resulted in adducts that undergoes a cyclization in water or DMF to form 5-fluoroalkyloxazoline with moderate yields. It was also found that the products can be more efficiently formed via an AIBN-initiated, one-pot addition-cyclization sequence from 1-allyl-3-arylurea with fluoroalkyl iodide.

同期刊论文项目
新型氟代HMG-CoA还原酶抑制剂的设计与合成
期刊论文 36 会议论文 4
手性偕二氟甲基噁唑烷酮的合成研究
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期刊信息
  • 《有机化学》
  • 中国科技核心期刊
  • 主管单位:
  • 主办单位:中国化学会 中国科学院上海有机化学研究所
  • 主编：陈庆云
  • 地址：上海市枫林路354号
  • 邮编：200032
  • 邮箱：bianji@mail.sioc.ac.cn
  • 电话：021-54925244
  • 国际标准刊号：ISSN：0253-2786
  • 国内统一刊号：ISSN：31-1321/O6
  • 邮发代号:4-285
  • 获奖情况:
  • 中国期刊方阵“双效”期刊
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘（网络版）,荷兰文摘与引文数据库,美国科学引文索引（扩展库）,日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊（2004版）,中国北大核心期刊（2008版）,中国北大核心期刊（2011版）,中国北大核心期刊（2014版）,中国北大核心期刊（2000版）
  • 被引量:14408