Literature DB >> 26035338

Direct Annulation of Hydrazides to 1,3,4-Oxadiazoles via Oxidative C(CO)-C(Methyl) Bond Cleavage of Methyl Ketones.

Qinghe Gao, Shan Liu, Xia Wu, Jingjing Zhang, Anxin Wu.   

Abstract

A new strategy for the synthesis of 1,3,4-oxadiazoles was established through direct annulation of hydrazides with methyl ketones. It was found that the use of K2CO3 as a base achieves an unexpected and highly efficient C-C bond cleavage. This reaction is proposed to go through oxidative cleavage of Csp(3)-H bonds, followed by cyclization and deacylation.

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Year:  2015        PMID： 26035338     DOI： 10.1021/acs.orglett.5b01241

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


  10 in total

1.  1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis.

Authors:  Kazuyuki Tokumaru; Kalisankar Bera; Jeffrey N Johnston
Journal:  Synthesis (Stuttg)       Date:  2017-08-07       Impact factor: 3.157

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.  Oxadiazol-based mTOR inhibitors with potent antiproliferative activities: synthetic and computational modeling.

Authors:  Mohammad A Khanfar
Journal:  Mol Divers       Date:  2022-01-05       Impact factor: 2.943

4.  A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.

Authors:  Kazuyuki Tokumaru; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2017-02-23       Impact factor: 9.825

5.  1,3,4-Oxadiazoles by Ugi-Tetrazole and Huisgen Reaction.

Authors:  Qian Wang; Kumchok C Mgimpatsang; Markella Konstantinidou; Svitlana V Shishkina; Alexander Dömling
Journal:  Org Lett       Date:  2019-09-03       Impact factor: 6.005

6.  Visible light-mediated photocatalytic oxidative cleavage of activated alkynes via hydroamination: a direct approach to oxamates.

Authors:  Narenderreddy Katta; Mamata Ojha; Arumugavel Murugan; Sagar Arepally; Duddu S Sharada
Journal:  RSC Adv       Date:  2020-03-27       Impact factor: 3.361

7.  KI-catalyzed oxidative cyclization of α-keto acids and 2-hydrazinopyridines: efficient one-pot synthesis of 1,2,4-triazolo[4,3-a]pyridines.

Authors:  De-Suo Yang; Juan Wang; Peng Gao; Zi-Jing Bai; Dong-Zhu Duan; Ming-Jin Fan
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

8.  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

9.  Electrophilic activation of nitroalkanes in efficient synthesis of 1,3,4-oxadiazoles.

Authors:  Alexander V Aksenov; Vladislav Khamraev; Nicolai A Aksenov; Nikita K Kirilov; Dmitriy A Domenyuk; Vladimir A Zelensky; Michael Rubin
Journal:  RSC Adv       Date:  2019-02-26       Impact factor: 3.361

10.  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
  10 in total

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