Literature DB >> 30576159

In Situ Generation of Nitrile Oxides from NaCl-Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition.

Guodong Zhao1, Lixin Liang1, Chi Ho Ethan Wen1, Rongbiao Tong1,2.   

Abstract

Reported is a new green protocol for the efficient in situ generation of nitrile oxides through NaCl/Oxone oxidation of aldoximes and their dipolar cycloaddition. The key feature is the use of a green chemistry approach to address the substrate scope of aldoximes: broad scope (aliphatic, aromatic, and alkenyl aldoximes) without production of organic byproducts derived from oxidant and/or catalyst. Importantly, NaCl/Oxone-promoted three-component cycloaddition of aldehyde, hydroxylamine hydrochloride, and alkene was demonstrated to be competent (63-81%).

Entities:  

Year:  2018        PMID： 30576159     DOI： 10.1021/acs.orglett.8b03829

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines.

Authors:  Kaikai Wang; Yanli Li; Wei Zhang; Rongxiang Chen; Xueji Ma; Mingyue Wang; Nan Zhou
Journal:  Molecules       Date:  2022-05-10       Impact factor: 4.927

2.  Mechanochemical Dimerization of Aldoximes to Furoxans.

Authors:  Run-Kai Fang; Kuan Chen; Chuang Niu; Guan-Wu Wang
Journal:  Molecules       Date:  2022-04-18       Impact factor: 4.927

3.  Enantioselective Total Synthesis of (+)-EBC-23, a Potent Anticancer Agent from the Australian Rainforest.

Authors:  Arun K Ghosh; Che-Sheng Hsu
Journal:  J Org Chem       Date:  2021-04-19       Impact factor: 4.354

4.  Reaction of Aldoximes with Sodium Chloride and Oxone under Ball-Milling Conditions.

Authors:  Kuan Chen; Chuang Niu; Guan-Wu Wang
Journal:  Molecules       Date:  2020-08-14       Impact factor: 4.411

5.  Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides.

Authors:  Md Imran Hossain; Md Imdadul H Khan; Seong Jong Kim; Hoang V Le
Journal:  Beilstein J Org Chem       Date:  2022-04-22       Impact factor: 2.544

6.  Facile synthesis of O-acylhydroxamates via reaction of oxime chlorides with carboxylic acids.

Authors:  Kai-Kai Wang; Yan-Li Li; Ying-Chao Zhao; Shan-Shan Zhang; Rongxiang Chen; Aili Sun
Journal:  RSC Adv       Date:  2021-12-20       Impact factor: 3.361

7.  Electrochemical Synthesis of Isoxazolines: Method and Mechanism.

Authors:  Samuel D L Holman; Alfie G Wills; Neal J Fazakerley; Darren L Poole; Diane M Coe; Leonard A Berlouis; Marc Reid
Journal:  Chemistry       Date:  2022-02-10       Impact factor: 5.020

8.  [2 + 2 + 1] Cycloaddition of N-tosylhydrazones, tert-butyl nitrite and alkenes: a general and practical access to isoxazolines.

Authors:  Liang Ma; Feng Jin; Xionglve Cheng; Suyan Tao; Gangzhong Jiang; Xingxing Li; Jinwei Yang; Xiaoguang Bao; Xiaobing Wan
Journal:  Chem Sci       Date:  2021-06-22       Impact factor: 9.825
  8 in total

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