Literature DB >> 22007797

Cu(II) catalyzed imine C-H functionalization leading to synthesis of 2,5-substituted 1,3,4-oxadiazoles.

Srimanta Guin1, Tuhin Ghosh, Saroj Kumar Rout, Arghya Banerjee, Bhisma K Patel.   

Abstract

A direct access to symmetrical and unsymmetrical 2,5-disubstituted [1,3,4]-oxadiazoles has been accomplished through an imine C-H functionalization of N-arylidenearoylhydrazide using a catalytic quantity of Cu(OTf)(2). This is the first example of amidic oxygen functioning as a nucleophile in a Cu-catalyzed oxidative coupling of an imine C-H bond. These reactions can be performed in air atmosphere and moisture making it exceptionally practical for application in organic synthesis.

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Year:  2011        PMID： 22007797     DOI： 10.1021/ol202409r

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


  9 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents.

Authors:  Elahe Yarmohammadi; Hamid Beyzaei; Reza Aryan; Ashraf Moradi
Journal:  Mol Divers       Date:  2020-08-08       Impact factor: 2.943

3.  Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action.

Authors:  Srinivas Angapelly; P V Sri Ramya; Rohini Sodhi; Andrea Angeli; Krishnan Rangan; Narayana Nagesh; Claudiu T Supuran; Mohammed Arifuddin
Journal:  J Enzyme Inhib Med Chem       Date:  2018-12       Impact factor: 5.051

4.  Additive-free photo-mediated oxidative cyclization of pyridinium acylhydrazones to 1,3,4-oxadiazoles: solid-state conversion in a microporous organic polymer and supramolecular energy-level engineering.

Authors:  Kyung-Su Kim; You Kyoung Chung; Hyunwoo Kim; Chae Yeon Ha; Joonsuk Huh; Changsik Song
Journal:  RSC Adv       Date:  2021-01-07       Impact factor: 3.361

5.  Copper-catalyzed intramolecular cross dehydrogenative coupling approach to coumestans from 2'-hydroxyl-3-arylcoumarins.

Authors:  Xianheng Song; Xiang Luo; Jianfei Sheng; Jianheng Li; Zefeng Zhu; Zhibo Du; Hui Miao; Meng Yan; Mingkang Li; Yong Zou
Journal:  RSC Adv       Date:  2019-06-03       Impact factor: 4.036

6.  The preparation, characterization and catalytic activity of Ni NPs supported on porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide).

Authors:  Sedigheh Alavinia; Ramin Ghorbani-Vaghei
Journal:  RSC Adv       Date:  2021-09-06       Impact factor: 3.361

7.  Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation.

Authors:  Chinnari Lekkala; Varaprasad Bodala; Kumari Yettula; Bharat Kumar Karasala; Rajitha Lakshmi Podugu; Siddaiah Vidavalur
Journal:  ACS Omega       Date:  2022-07-27

8.  Synthesis of 2-Imino-1,3,4-oxadiazolines from Acylhydrazides and Isothiocyanates via Aerobic Oxidation and a DMAP-Mediated Annulation Sequence.

Authors:  Jae Hyeok Lim; Sang Eun Baek; Bapurao Sudam Lad; Jinho Kim
Journal:  ACS Omega       Date:  2022-08-01

Review 9.  Synthetic approaches and pharmacological activity of 1,3,4-oxadiazoles: a review of the literature from 2000-2012.

Authors:  Cledualdo Soares de Oliveira; Bruno Freitas Lira; José Maria Barbosa-Filho; Jorge Gonçalo Fernandez Lorenzo; Petrônio Filgueiras de Athayde-Filho
Journal:  Molecules       Date:  2012-08-27       Impact factor: 4.411
  9 in total

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