Literature DB >> 25873036

Regioselective syntheses of 1,2-benzothiazines by rhodium-catalyzed annulation reactions.

Ying Cheng1, Carsten Bolm2.   

Abstract

Rhodium-catalyzed directed carbene insertions into aromatic CH bonds of S-aryl sulfoximines lead to intermediates, which upon dehydration provide 1,2-benzothiazines in excellent yields. The domino-type process is regioselective and shows a high functional-group tolerance. It is scalable, and the only by-products are dinitrogen and water. Three illustrative transformations underscore the synthetic value of the products.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; carbenes; diazo compounds; heterocycles; rhodium

Mesh：

Substances：

Year:  2015        PMID： 25873036     DOI： 10.1002/anie.201501583

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Stereospecific α-(hetero)arylation of sulfoximines and sulfonimidamides.

Authors:  Zachary P Shultz; Thomas Scattolin; Lukasz Wojtas; Justin M Lopchuk
Journal:  Nat Synth       Date:  2022-01-31

Review 2.  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

3.  Insights into the Activation Mode of α-Carbonyl Sulfoxonium Ylides in Rhodium-Catalyzed C-H Activation: A Theoretical Study.

Authors:  Dianmin Zhang; Xiaofang He; Tao Yang; Song Liu
Journal:  ChemistryOpen       Date:  2022-02-24       Impact factor: 2.630

4.  Rh(III)-Catalyzed C-H Activation/Intramolecular Cyclization: Access to N-Acyl-2,3-dihydro-1H-carbazol-4(9H)-ones from Cyclic 2-Diazo-1,3-diketones and N-Arylamides.

Authors:  Youpeng Zuo; Xinwei He; Yi Ning; Yuhao Wu; Yongjia Shang
Journal:  ACS Omega       Date:  2017-11-30

5.  Basicity-Tuned Reactivity: diaza-[1,2]-Wittig versus diaza-[1,3]-Wittig Rearrangements of 3,4-Dihydro-2H-1,2,3-benzothiadiazine 1,1-Dioxides.

Authors:  Imre Gyűjtő; Márta Porcs-Makkay; Gergő Szabó; Zsolt Kelemen; Gyöngyvér Pusztai; Gábor Tóth; András Dancsó; Judit Halász; Gyula Simig; Balázs Volk; László Nyulászi
Journal:  J Org Chem       Date:  2020-12-31       Impact factor: 4.354

6.  Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides.

Authors:  Marina Zenzola; Robert Doran; Leonardo Degennaro; Renzo Luisi; James A Bull
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-29       Impact factor: 15.336

7.  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
  7 in total

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