Literature DB >> 14986989

Synthesis of substituted imidazoles via organocatalysis.

Doug E Frantz1, Louis Morency, Arash Soheili, Jerry A Murry, Edward J J Grabowski, Richard D Tillyer.   

Abstract

A one-pot synthesis of substituted imidazoles is described. The cornerstone of this methodology involves the thiazolium-catalyzed addition of an aldehyde to an acyl imine to generate the corresponding alpha-ketoamide in situ followed by ring closure to the imidazole in a one-pot sequence. The extension of this methodology to the one-pot synthesis of substituted oxazoles and thiazoles is also described. [reaction: see text]

Entities:  

Year:  2004        PMID: 14986989     DOI: 10.1021/ol0498803

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


  9 in total

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Authors:  Jennifer L Moore; Tomislav Rovis
Journal:  Top Curr Chem       Date:  2010

2.  Two step syntheses of fused quinoxaline-benzodiazepines and bis-benzodiazepines.

Authors:  Zhigang Xu; Justin Dietrich; Arthur Y Shaw; Christopher Hulme
Journal:  Tetrahedron Lett       Date:  2010-08-25       Impact factor: 2.415

3.  C-H bonds as ubiquitous functionality: a general approach to complex arylated imidazoles via regioselective sequential arylation of all three C-H bonds and regioselective N-alkylation enabled by SEM-group transposition.

Authors:  Jung Min Joo; B Barry Touré; Dalibor Sames
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

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.  Supported heteropoly acids offering strong option for efficient and cleaner processing for the synthesis of imidazole derivatives under solvent-free condition.

Authors:  Ezzat Rafiee; Houri Mahdavi; Mohammad Joshaghani
Journal:  Mol Divers       Date:  2010-01-26       Impact factor: 2.943

6.  N-Heterocyclic carbene-catalyzed direct cross-aza-benzoin reaction: Efficient synthesis of α-amino-β-keto esters.

Authors:  Takuya Uno; Yusuke Kobayashi; Yoshiji Takemoto
Journal:  Beilstein J Org Chem       Date:  2012-09-10       Impact factor: 2.883

7.  Radical cascade reaction of alkynes with N-fluoroarylsulfonimides and alcohols.

Authors:  Guangfan Zheng; Yan Li; Jingjie Han; Tao Xiong; Qian Zhang
Journal:  Nat Commun       Date:  2015-04-22       Impact factor: 14.919

8.  Investigation on the reactivity of α-azidochalcones with carboxylic acids: Formation of α-amido-1,3-diketones and highly substituted 2-(trifluoromethyl)oxazoles.

Authors:  Kandasamy Rajaguru; Arumugam Mariappan; Rajendran Suresh; Periasamy Manivannan; Shanmugam Muthusubramanian
Journal:  Beilstein J Org Chem       Date:  2015-10-29       Impact factor: 2.883

9.  One-Step Synthesis of 2,5-Diaminoimidazoles and Total Synthesis of Methylglyoxal-Derived Imidazolium Crosslink (MODIC).

Authors:  Venkata R Sabbasani; Kung-Pern Wang; Matthew D Streeter; David A Spiegel
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-12       Impact factor: 15.336

  9 in total

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