Literature DB >> 30964689

Gold(III)-Catalyzed Formal [3 + 2] Annulations of N-Acyl Sulfilimines with Ynamides for the Synthesis of 4-Aminooxazoles.

Xianhai Tian1, Lina Song1, Chunyu Han1, Cheng Zhang1, Yufeng Wu1, Matthias Rudolph1, Frank Rominger1, A Stephen K Hashmi1,2.   

Abstract

A gold-catalyzed formal 1,3-dipolar [3 + 2] annulation using readily accessible N-acyl sulfilimines and n class="Chemical">ynamides is reported. This reaction includes the cleavage of a N-S bond and subsequent C-O bond formation. In total, 30 oxazole derivatives bearing diverse functionalities could be prepared in 43-98% yield from the corresponding sulfilimines and ynamides.

Entities:  

Year:  2019        PMID: 30964689     DOI: 10.1021/acs.orglett.9b01011

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


  4 in total

1.  Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Authors:  Peter E Simm; Prakash Sekar; Jeffery Richardson; Paul W Davies
Journal:  ACS Catal       Date:  2021-05-13       Impact factor: 13.084

2.  AgNTf2-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives.

Authors:  Ziping Cao; Jiekun Zhu; Li Liu; Yuanling Pang; Laijin Tian; Xuejun Sun; Xin Meng
Journal:  Beilstein J Org Chem       Date:  2019-11-04       Impact factor: 2.883

3.  Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.

Authors:  Xianhai Tian; Lina Song; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-02       Impact factor: 15.336

4.  Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.

Authors:  Xianhai Tian; Lina Song; Kaveh Farshadfar; Matthias Rudolph; Frank Rominger; Thomas Oeser; Alireza Ariafard; A Stephen K Hashmi
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-26       Impact factor: 15.336

  4 in total

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