Literature DB >> 33483530

Mild synthesis of isoxazoline derivatives via an efficient [4 + 1] annulation reaction of transient nitrosoalkenes and sulfur ylides.

Ting-Bi Hua1,2, Cheng-Xiong Liu2, Wei-Min Hu1, Long Wang3, Qing-Qing Yang4,5.   

Abstract

An efficient [4 + 1] annulation between α-bromooximes and sulfur ylides via in situ generation of nitrosoalkenes under mild basic reaction conditions has been developed, providing an expeditious and scalable approach to synthesize biologically interesting isoxazoline derivatives with good to excellent yields.

Entities:  

Year:  2021        PMID: 33483530     DOI: 10.1038/s41598-021-81370-w

Source DB:  PubMed          Journal:  Sci Rep        ISSN: 2045-2322            Impact factor:   4.379


  21 in total

Review 1.  Chemistry of six-membered cyclic oxime ethers. Application in the synthesis of bioactive compounds.

Authors:  Alexey Yu Sukhorukov; Sema L Ioffe
Journal:  Chem Rev       Date:  2011-03-24       Impact factor: 60.622

2.  Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems.

Authors:  Jia-Rong Chen; Xiao-Qiang Hu; Liang-Qiu Lu; Wen-Jing Xiao
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

3.  An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes.

Authors:  Pankaj V Khairnar; Tsai-Hui Lung; Yi-Jung Lin; Chi-Yi Wu; Srinivasa Rao Koppolu; Athukuri Edukondalu; Praneeth Karanam; Wenwei Lin
Journal:  Org Lett       Date:  2019-05-22       Impact factor: 6.005

4.  Recent Advances in the Chemistry of Conjugated Nitrosoalkenes and Azoalkenes.

Authors:  Susana M M Lopes; Ana L Cardoso; Américo Lemos; Teresa M V D Pinho E Melo
Journal:  Chem Rev       Date:  2018-11-29       Impact factor: 60.622

5.  Beyond sulfide-centric catalysis: recent advances in the catalytic cyclization reactions of sulfur ylides.

Authors:  Liang-Qiu Lu; Tian-Ren Li; Qiang Wang; Wen-Jing Xiao
Journal:  Chem Soc Rev       Date:  2017-07-17       Impact factor: 54.564

6.  Enantioselective synthesis of dihydropyrazoles by formal [4+1] cycloaddition of in situ-derived azoalkenes and sulfur ylides.

Authors:  Jia-Rong Chen; Wan-Rong Dong; Mathieu Candy; Fang-Fang Pan; Manuel Jörres; Carsten Bolm
Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

7.  Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes.

Authors:  Yana A Naumovich; Sema L Ioffe; Alexey Yu Sukhorukov
Journal:  J Org Chem       Date:  2019-05-15       Impact factor: 4.354

8.  Construction of optically active indolines by formal [4+1] annulation of sulfur ylides and N-(ortho-chloromethyl)aryl amides.

Authors:  Qing-Qing Yang; Qiang Wang; Jing An; Jia-Rong Chen; Liang-Qiu Lu; Wen-Jing Xiao
Journal:  Chemistry       Date:  2013-05-13       Impact factor: 5.236

9.  A new entry to cascade organocatalysis: reactions of stable sulfur ylides and nitroolefins sequentially catalyzed by thiourea and DMAP.

Authors:  Liang-Qiu Lu; Yi-Ju Cao; Xiao-Peng Liu; Jing An; Chang-Jiang Yao; Zhi-Hui Ming; Wen-Jing Xiao
Journal:  J Am Chem Soc       Date:  2008-05-13       Impact factor: 15.419

10.  Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes.

Authors:  Olivier Rousseau; Thierry Delaunay; Geoffroy Dequirez; Tran Trieu-Van; Koen Robeyns; Raphaël Robiette
Journal:  Chemistry       Date:  2015-07-31       Impact factor: 5.236

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