Literature DB >> 27388581

Synthesis of 1,2-Benzothiazines by a Rhodium-Catalyzed Domino C-H Activation/Cyclization/Elimination Process from S-Aryl Sulfoximines and Pyridotriazoles.

Woo Hyung Jeon1, Jeong-Yu Son1, Ji Eun Kim1, Phil Ho Lee1.   

Abstract

A method for the synthesis of a large number of 1,2-benzothiazines bearing pyridyl as well as carbonyl groups is developed from n class="Chemical">rhodium-catalyzed carbene insertions into aromatic C-H bonds of S-aryl sulfoximines using pyridotriazoles by denitrogenative cyclization followed by the elimination of alcohols. The present method involves the N-H/C-H activation of simple alkyl aryl sulfoximines and has the advantages of a broad substrate scope, high functional group tolerance, and good regioselectivity.

Entities:  

Year:  2016        PMID: 27388581     DOI: 10.1021/acs.orglett.6b01750

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


  4 in total

Review 1.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

2.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

3.  Ru(ii)-catalyzed C6-selective C-H acylmethylation of pyridones using sulfoxonium ylides as carbene precursors.

Authors:  Yangjie Fu; Zhaohui Wang; Qiyu Zhang; Zhiyu Li; Hong Liu; Xiaoling Bi; Jiang Wang
Journal:  RSC Adv       Date:  2020-02-11       Impact factor: 4.036

4.  Sulfoximines-Assisted Rh(III)-Catalyzed C-H Activation and Intramolecular Annulation for the Synthesis of Fused Isochromeno-1,2-Benzothiazines Scaffolds under Room Temperature.

Authors:  Bao Wang; Xu Han; Jian Li; Chunpu Li; Hong Liu
Journal:  Molecules       Date:  2020-05-28       Impact factor: 4.411

  4 in total

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