Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores

  • Park, Sang Won; 
  • Kim, Soong-Hyun; 
  • Song, Jaeyoung; 
  • Park, Ga Young; 
  • Kim, Darong; 
  • ... Nam, Tae-Gyu; 
  • 외 1명
Citations

WEB OF SCIENCE

11
Citations

SCOPUS

12

초록

Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)(2) ((diacetoxyiodo) benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to accessing both isoxazoline and pyrazoline cores. Additionally, acetonitrile serves as both the solvent and an amine source in the presence of this PIDA/Lewis acid combination. This operationally straightforward and metal-free protocol provides an easy access to isoxazoline and pyrazoline derivatives.

키워드

amido-amidation; hypervalent iodine; isoxazoline; metal-free; oxyamidation; pyrazoline; ELECTRON-RICH AMINES; BETA,GAMMA-UNSATURATED OXIMES; UNACTIVATED ALKENES; FACILE SYNTHESIS; CYCLIC NITRONES; DIAMINATION; CYCLIZATIONS; DERIVATIVES; MOLECULES
제목
Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
저자
Park, Sang Won; Kim, Soong-Hyun; Song, Jaeyoung; Park, Ga Young; Kim, Darong; Nam, Tae-Gyu; Hong, Ki Bum
DOI
10.3762/bjoc.14.89
발행일
2018-05
유형
Article
저널명
Beilstein Journal of Organic Chemistry
권
14
페이지
1028 ~ 1033

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