Literature DB >> 16910644

Synthesis of imidazoles through the copper-catalyzed cross-cycloaddition between two different isocyanides.

Chikashi Kanazawa1, Shin Kamijo, Yoshinori Yamamoto.   

Abstract

The copper-catalyzed reaction between two different isocyanides produces the corresponding heteroaromatization products, imidazoles, in good yields. The reaction proceeds most probably through the activation of the sp3 C-H bond in the isocyanides by a copper catalyst, followed by a [3 + 2] cycloaddition between the cuprioisocyanide intermediates and arylisocyanides.

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Year:  2006        PMID: 16910644     DOI: 10.1021/ja0617439

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


  8 in total

1.  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

2.  Catalytic Isonitrile Insertions and Condensations Initiated by RNC-X Complexation.

Authors:  Suravi Chakrabarty; Shruti Choudhary; Arpit Doshi; Fa-Qiang Liu; Rishabh Mohan; Manasa P Ravindra; Dhruv Shah; Xun Yang; Fraser F Fleming
Journal:  Adv Synth Catal       Date:  2014-06-20       Impact factor: 5.837

3.  Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors:  Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Org Chem       Date:  2007-04-12       Impact factor: 4.354

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.  Silver-Assisted [3 + 2] Annulation of Nitrones with Isocyanides: Synthesis of 2,3,4-Trisubstituted 1,2,4-Oxadiazolidin-5-ones.

Authors:  Xuanyu Shen; Andrey Shatskiy; Yan Chen; Markus D Kärkäs; Xiang-Shan Wang; Jian-Quan Liu
Journal:  J Org Chem       Date:  2020-02-20       Impact factor: 4.354

6.  Unusual light-driven amplification through unexpected regioselective photogeneration of five-membered azaheterocyclic AIEgen.

Authors:  Qiyao Li; Junyi Gong; Ying Li; Ruoyao Zhang; Haoran Wang; Jianquan Zhang; He Yan; Jacky W Y Lam; Herman H Y Sung; Ian D Williams; Ryan T K Kwok; Min-Hui Li; Jianguo Wang; Ben Zhong Tang
Journal:  Chem Sci       Date:  2020-10-19       Impact factor: 9.825

7.  Aroylketene dithioacetal chemistry: facile synthesis of 4-aroyl-3-methylsulfanyl-2-tosylpyrroles from aroylketene dithioacetals and TosMIC.

Authors:  H Surya Prakash Rao; S Sivakumar
Journal:  Beilstein J Org Chem       Date:  2007-09-28       Impact factor: 2.883

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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