Literature DB >> 28650165

1,3-Dipolar Cycloaddition of Nitrile Imine with Carbon Dioxide: Access to 1,3,4-Oxadiazole-2(3H)-ones.

Chun-Xiao Guo1, Wen-Zhen Zhang1, Ning Zhang1, Xiao-Bing Lu1.   

Abstract

Efficient synthesis of 1,3,4-oxadiazole-2(3H)-one was achieved by CsF/18-crown-6 mediated 1,3-dipolar cycloaddition of nitrile imine and 2.0 MPa of CO2. CsF/18-crown-6 played a key role in enhancing the reactivity of CO2 as a 1,3-dipolarophile. The practical utility of this transition-metal-free approach to 1,3,4-oxadiazole-2(3H)-one is highlighted by the convenient synthesis of a commercial herbicide Oxadiazon and a MAO B inhibitor.

Entities:  

Year:  2017        PMID： 28650165     DOI： 10.1021/acs.joc.7b00963

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  How the Lewis Base F- Catalyzes the 1,3-Dipolar Cycloaddition between Carbon Dioxide and Nitrilimines.

Authors:  Dennis Svatunek; Thomas Hansen; Kendall N Houk; Trevor A Hamlin
Journal:  J Org Chem       Date:  2021-02-12       Impact factor: 4.354

2.  Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides.

Authors:  Mhairi Boyle; Keith Livingstone; Martyn C Henry; Jessica M L Elwood; J Daniel Lopez-Fernandez; Craig Jamieson
Journal:  Org Lett       Date:  2021-12-29       Impact factor: 6.005

3.  Synthesis of spiro[4.4]thiadiazole derivatives via double 1,3-dipolar cycloaddition of hydrazonyl chlorides with carbon disulfide.

Authors:  Kai-Kai Wang; Yan-Li Li; Dong-Guang Guo; Peng-Tao Pan; Aili Sun; Rongxiang Chen
Journal:  RSC Adv       Date:  2021-05-21       Impact factor: 4.036
  3 in total

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