Literature DB >> 28218539

α-Imino Gold Carbenes from 1,2,4-Oxadiazoles: Atom-Economical Access to Fully Substituted 4-Aminoimidazoles.

Zhongyi Zeng1, Hongming Jin1, Jin Xie1, Bing Tian1, Matthias Rudolph1, Frank Rominger1, A Stephen K Hashmi1,2.   

Abstract

A novel and atom-economical synthesis of fully substituted 4-aminoimidazoles via gold-catalyzed selective [3 + 2] annulation of 1,2,4-oxadiazoles with ynamides is reported. This protocol represents a new strategy to access α-imino gold carbenes, which corresponds to an unprecedented intermolecular transfer of N-acylimino nitrenes to ynamides. Moreover, the reaction proceeds with 100% atom economy, exhibits good functional group tolerance, and can be conducted in gram scale.

Entities:  

Year:  2017        PMID: 28218539     DOI: 10.1021/acs.orglett.7b00001

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


  9 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.  Structure and Reactivity of Highly Twisted N-Acylimidazoles.

Authors:  Elizabeth A Stone; Brandon Q Mercado; Scott J Miller
Journal:  Org Lett       Date:  2019-03-12       Impact factor: 6.005

Review 3.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

4.  Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles.

Authors:  Giovanni Di Mauro; Boris Maryasin; Daniel Kaiser; Saad Shaaban; Leticia González; Nuno Maulide
Journal:  Org Lett       Date:  2017-07-13       Impact factor: 6.005

5.  Synthesis of poly-functionalized benzofurans via one-pot domino oxidation/[3+2] cyclization reactions of a hydroquinone ester and ynamides.

Authors:  Dongxin Zhang; Jingjing Man; Yan Chen; Lei Yin; Junchao Zhong; Qian-Feng Zhang
Journal:  RSC Adv       Date:  2019-04-25       Impact factor: 4.036

6.  Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl cations.

Authors:  Sovan Sundar Giri; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-02-19       Impact factor: 9.825

7.  Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles.

Authors:  Raju Jannapu Reddy; Matthew P Ball-Jones; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-19       Impact factor: 15.336

8.  Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups.

Authors:  Bhanudas Dattatray Mokar; Prakash D Jadhav; Y B Pandit; Rai-Shung Liu
Journal:  Chem Sci       Date:  2018-04-23       Impact factor: 9.825

9.  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

  9 in total

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