Literature DB >> 16669670

A direct, one step synthesis of imidazoles from imines and acid chlorides: a palladium catalyzed multicomponent coupling approach.

Ali R Siamaki1, Bruce A Arndtsen.   

Abstract

A palladium-catalyzed one-step synthesis of imidazoles from imines and acid chlorides is described. A plausible mechanism for this multicomponent reaction is provided, which explains the selective incorporation of two different imines into the final product with perfect regiocontrol. Overall, this catalytic process provides a modular method to prepare imidazoles directly from building blocks that are all either commercially available or readily generated.

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Year:  2006        PMID： 16669670     DOI： 10.1021/ja060705m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

1.  Diastereoselective synthesis of fused [1,3]oxazines from ethyl pyruvate, activated acetylenes and N-heterocycles.

Authors:  Issa Yavari; Anvar Mirzaei; Zinatosadat Hossaini; Sanaz Souri
Journal:  Mol Divers       Date:  2009-07-04       Impact factor: 2.943

2.  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

3.  A palladium-catalyzed synthesis of (hetero)aryl-substituted imidazoles from aryl halides, imines and carbon monoxide.

Authors:  Jevgenijs Tjutrins; Bruce A Arndtsen
Journal:  Chem Sci       Date:  2016-11-03       Impact factor: 9.825

4.  Polysubstituted Imidazoles as LysoTracker Molecules: Their Synthesis via Iodine/H2O and Cell-Imaging Studies.

Authors:  Saswati Adhikary; Leena Majumder; Sourav Pakrashy; Ravuri Srinath; Kaustuv Mukherjee; Chitra Mandal; Biswadip Banerji
Journal:  ACS Omega       Date:  2020-06-11

5.  Visible Light-Promoted Green and Sustainable Approach for One-Pot Synthesis of 4,4'-(Arylmethylene)bis(1H-pyrazol-5-ols), In Vitro Anticancer Activity, and Molecular Docking with Covid-19 Mpro.

Authors:  Anamika Gupta; Safia Iqbal; Mohd Kamil Hussain; Mohd Rehan Zaheer; Krapa Shankar
Journal:  ACS Omega       Date:  2022-09-14

6.  Palladium-catalyzed multicomponent synthesis of 2-imidazolines from imines and acid chlorides.

Authors:  Boran Xu; Kraig Worrall; Bruce A Arndtsen
Journal:  Molecules       Date:  2012-11-22       Impact factor: 4.411

Review 7.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457

8.  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
  8 in total

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