Literature DB >> 28138199

Rapid, Microwave Accelerated Synthesis of [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazoles from 4-Acylamino-1,2,4-Triazoles.

Stesphanie L Breunig1, Margaret E Olson1, Daniel A Harki1.   

Abstract

1,2,4-Triazoles and 1,3,4-oxadiazoles are prevalent moieties in pharmaceutical agents, yet fused [1,2,4]-triazolo[3,4-b][1,3,4]oxadiazoles are surprisingly under-represented for both synthesis and biological application. We report a rapid, two-step synthesis of [1,2,4]-triazolo[3,4-b][1,3,4]oxadiazoles from commercial 4-amino-1,2,4-triazoles that is highlighted by a microwave accelerated intramolecular cyclization to generate the fused ring system. Our efforts to optimize reaction conditions and elucidate reaction mechanism are also described.

Entities:  

Keywords:  1,2,4-Triazole; 1,3,4-Oxadiazole; Intramolecular Cyclization; Microwave Chemistry; [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazole

Year:  2016        PMID: 28138199      PMCID: PMC5271595          DOI: 10.1016/j.tetlet.2016.07.082

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  23 in total

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Journal:  Bioorg Med Chem Lett       Date:  2006-07-28       Impact factor: 2.823

2.  Synthesis of 2-arylbenzoxazoles by copper-catalyzed intramolecular oxidative C-O coupling of benzanilides.

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Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Development of nitrile-based peptidic inhibitors of cysteine cathepsins.

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Journal:  Curr Top Med Chem       Date:  2010       Impact factor: 3.295

4.  Derivatives of benzimidazole pharmacophore: synthesis, anticonvulsant, antidiabetic and DNA cleavage studies.

Authors:  Ramya V Shingalapur; Kallappa M Hosamani; Rangappa S Keri; Mallinath H Hugar
Journal:  Eur J Med Chem       Date:  2010-01-14       Impact factor: 6.514

5.  Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2-thiazolyl)acetamido]thio-4H-1,2,4-triazole derivatives.

Authors:  Gülhan Turan-Zitouni; Zafer Asim Kaplancikli; Mehmet Taha Yildiz; Pierre Chevallet; Demet Kaya
Journal:  Eur J Med Chem       Date:  2005-03-02       Impact factor: 6.514

Review 6.  1,3,4-Oxadiazoles: An emerging scaffold to target growth factors, enzymes and kinases as anticancer agents.

Authors:  Shalini Bajaj; Vivek Asati; Jagadish Singh; Partha Pratim Roy
Journal:  Eur J Med Chem       Date:  2015-04-27       Impact factor: 6.514

7.  Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents.

Authors:  Qian-Ru Du; Dong-Dong Li; Ya-Zhou Pi; Jing-Ran Li; Jian Sun; Fei Fang; Wei-Qing Zhong; Hai-Bin Gong; Hai-Liang Zhu
Journal:  Bioorg Med Chem       Date:  2013-02-19       Impact factor: 3.641

8.  Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents.

Authors:  Ashraf Hassan Abadi; Amal Abdel Haleem Eissa; Ghaneya Sayed Hassan
Journal:  Chem Pharm Bull (Tokyo)       Date:  2003-07       Impact factor: 1.645

9.  Synthesis and antiviral evaluation of novel 5-(N-Aryl-aminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and their sugars, 1,2,4-triazoles, tetrazoles and pyrazolyl derivatives.

Authors:  Mohammed T Abdel-Aal; Waled A El-Sayed; Salah M El-Kosy; El Sayed H El-Ashry
Journal:  Arch Pharm (Weinheim)       Date:  2008-05       Impact factor: 3.751

10.  Small-molecule APOBEC3G DNA cytosine deaminase inhibitors based on a 4-amino-1,2,4-triazole-3-thiol scaffold.

Authors:  Margaret E Olson; Ming Li; Reuben S Harris; Daniel A Harki
Journal:  ChemMedChem       Date:  2012-11-23       Impact factor: 3.466

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