Literature DB >> 24839436

Gold Catalysed Redox Synthesis of Imidazo[1,2-a]pyridine using Pyridine N-Oxide and Alkynes.

Eric P A Talbot1, Melodie Richardson2, Jeffrey M McKenna2, F Dean Toste3.   

Abstract

A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic PicAuCl2 in the presence of an acid produces a range imidazo[1,2-a]pyridines in good yield. This strategy is mild and forseen to be of particular use for the installation of stereogenic centers adjacent to the imidazo[1,2-a]pyridine ring without loss of enantiomeric excess.

Entities:  

Keywords:  alkyne; atom economic; gold; imidazo[1,2-a]pyridine; pyridine N-oxide; redox

Year:  2014        PMID： 24839436      PMCID： PMC4019451          DOI： 10.1002/adsc.201300996

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  30 in total

1.  Imidazo[1,2-a]pyridines susceptible to excited state intramolecular proton transfer: one-pot synthesis via an Ortoleva-King reaction.

Authors:  Anton J Stasyuk; Marzena Banasiewicz; Michał K Cyrański; Daniel T Gryko
Journal:  J Org Chem       Date:  2012-06-11       Impact factor: 4.354

2.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

3.  Metal-free oxidation/C(sp3)-H functionalization of unactivated alkynes using pyridine-N-oxide as the external oxidant.

Authors:  Dian-Feng Chen; Zhi-Yong Han; Yu-Ping He; Jie Yu; Liu-Zhu Gong
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-26       Impact factor: 15.336

4.  An efficient [2 + 2 + 1] synthesis of 2,5-disubstituted oxazoles via gold-catalyzed intermolecular alkyne oxidation.

Authors:  Weimin He; Chaoqun Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

5.  Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.

Authors:  Longwu Ye; Weimin He; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-06-30       Impact factor: 15.419

6.  Imidazo(1,2-a)pyridine anthelmintic and antifungal agents.

Authors:  M H Fisher; A Lusi
Journal:  J Med Chem       Date:  1972-09       Impact factor: 7.446

7.  Gold-catalyzed 1,2-difunctionalizations of aminoalkynes using only N- and O-containing oxidants.

Authors:  Anupam Mukherjee; Ramesh B Dateer; Rupsha Chaudhuri; Sabyasachi Bhunia; Somnath Narayan Karad; Rai-Shung Liu
Journal:  J Am Chem Soc       Date:  2011-09-12       Impact factor: 15.419

8.  Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

Authors:  Longwu Ye; Li Cui; Guozhu Zhang; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-03-17       Impact factor: 15.419

9.  2-Amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imid azo[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus: stereospecific synthesis and antiviral activity.

Authors:  C Hamdouchi; J de Blas; M del Prado; J Gruber; B A Heinz; L Vance
Journal:  J Med Chem       Date:  1999-01-14       Impact factor: 7.446

10.  Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles.

Authors:  Hyun-Suk Yeom; Youngun Lee; Ji-Eun Lee; Seunghoon Shin
Journal:  Org Biomol Chem       Date:  2009-09-01       Impact factor: 3.876
View more
  6 in total

1.  Gold-catalyzed Fluorination of Alkynyl Esters and Ketones: Efficient Access to Fluorinated 1,3-Dicarbonyl Compounds.

Authors:  Xiaojun Zeng; Zhichao Lu; Shiwen Liu; Gerald B Hammond; Bo Xu
Journal:  Adv Synth Catal       Date:  2017-10-05       Impact factor: 5.837

Review 2.  Homogeneous Gold-Catalyzed Oxidation Reactions.

Authors:  Zhitong Zheng; Xu Ma; Xinpeng Cheng; Ke Zhao; Kaylaa Gutman; Tianyou Li; Liming Zhang
Journal:  Chem Rev       Date:  2021-02-16       Impact factor: 72.087

3.  Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.

Authors:  Ai-Hua Zhou; Qiao He; Chao Shu; Yong-Fei Yu; Shuang Liu; Tian Zhao; Wei Zhang; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825

4.  One-Pot NBS-Promoted Synthesis of Imidazoles and Thiazoles from Ethylarenes in Water.

Authors:  Liang Chen; Huajian Zhu; Jiang Wang; Hong Liu
Journal:  Molecules       Date:  2019-03-04       Impact factor: 4.411

5.  A multi pathway coupled domino strategy: I2/TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization.

Authors:  Yishou Wang; Shichen Li; Xinfeng Wang; Yiming Yao; Lei Feng; Chen Ma
Journal:  RSC Adv       Date:  2022-02-17       Impact factor: 3.361

6.  Enantioselective synthesis of Iboga alkaloids and vinblastine via rearrangements of quaternary ammoniums.

Authors:  Yun Zhang; Yibin Xue; Gang Li; Haosen Yuan; Tuoping Luo
Journal:  Chem Sci       Date:  2016-05-16       Impact factor: 9.825
  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.