有机化学 ›› 2018, Vol. 38 ›› Issue (8): 1993-2001.DOI: 10.6023/cjoc201803054 上一篇    下一篇

研究论文

氨甲酰基硅烷作为氨酰基源合成α-磺酰氨基酰胺衍生物

韩宇玲, 仝文婷, 刘慧, 陈建新   

  1. 山西师范大学化学与材料科学学院 临汾 041004
  • 收稿日期:2018-03-30 修回日期:2018-05-13 出版日期:2018-08-25 发布日期:2018-05-24
  • 通讯作者: 陈建新 E-mail:jjxxcc2002@yahoo.com
  • 基金资助:

    山西省留学回国人员基金(No.0713)、山西省自然科学基金(No.2012011046-9)和山西师范大学文理学院基金(No.WL2016CXCY-YJ-30)资助项目.

Synthesis of α-(N-Sulfonyl)amino Amides Derivatives Using Carbamoylsilanes as an Amide Source

Han Yuling, Tong Wenting, Liu Hui, Chen Jianxin   

  1. College of Chemistry and Material Science, Shanxi Normal University, Linfen 041004
  • Received:2018-03-30 Revised:2018-05-13 Online:2018-08-25 Published:2018-05-24
  • Contact: 10.6023/cjoc201803054 E-mail:jjxxcc2002@yahoo.com
  • Supported by:

    Project supported by the Shanxi Provincal Foundation for Returness Overseas Scientists (No. 0713), the Natural Science Foundation of Shanxi Province (No. 2012011046-9), and the Foundation of the Modern College of Arts and Science, Shanxi Normal University (No. WL2016CXCY-YJ-30).

氨甲酰基硅烷与N-磺酰亚胺在无催化剂苯作溶剂的条件下反应,直接合成了磺酰基保护的α-氨基酰胺衍生物,收率为71%~89%.该方法不仅可合成α-氨基叔酰胺,还可合成α-氨基仲酰胺.通过研究反应的影响因素发现,N-磺酰亚胺双键相连基团旳电子效应是影响反应的重要因素,它既影响反应完成的时间,又影响产物的产率.该反应具有条件温和、副产物少、产率高和后处理简单等优点,是有效合成α-氨基酰胺的新方法.

关键词: 氨甲酰基硅烷, α-氨基酰胺, N-磺酰亚胺, 亲核加成, 合成方法

α-(N-Sulfonyl)amino amide derivatives are directly synthesized in 71%~89% yields by the reaction of carbamoylsilanes with various N-sulfonylimines in benzene under catalyst-free conditions. The procedure can prepare both tertiary and secondary α-amino amides. A comparison of the results obtained from the N-sulfonylimines containing the variety of alkyl, aryl and heterocyclic ring indicated that the electronic effect was an important factor in the addition reaction, which influenced on the rate and yields of the reaction. The new method is simple and mild procedure, no catalysts conditions, less byproducts and good yields for the preparation of α-aminoamides.

Key words: carbamoylsilane, α-amino amide, N-sulfonylimine, nucleophilic addition, synthetic method