Literature DB >> 32786060

UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow.

Luke Green1,2, Keith Livingstone1, Sophie Bertrand2, Simon Peace2, Craig Jamieson1.   

Abstract

A range of 1,3,4-oxadiazoles have been synthesized using a UV-B activated flow approach starting from carboxylic acids and 5-substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids.
© 2020 The Authors. Published by Wiley-VCH GmbH.

Entities:  

Keywords:  Huisgen reaction; flow; heterocycles; nitrile imines; photochemistry

Year:  2020        PMID： 32786060      PMCID： PMC7756889          DOI： 10.1002/chem.202002896

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  15 in total

1.  Bioisosterism: A Rational Approach in Drug Design.

Authors:  George A. Patani; Edmond J. LaVoie
Journal:  Chem Rev       Date:  1996-12-19       Impact factor: 60.622

2.  Chemical selectivity through control of excited-state dynamics.

Authors:  Massimo Olivucci; Fabrizio Santoro
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment.

Authors:  Dario Cambié; Cecilia Bottecchia; Natan J W Straathof; Volker Hessel; Timothy Noël
Journal:  Chem Rev       Date:  2016-03-03       Impact factor: 60.622

4.  Oxadiazoles in medicinal chemistry.

Authors:  Jonas Boström; Anders Hogner; Antonio Llinàs; Eric Wellner; Alleyn T Plowright
Journal:  J Med Chem       Date:  2012-01-13       Impact factor: 7.446

5.  Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity.

Authors:  Sumit Bansal; Manju Bala; Sharad Kumar Suthar; Shivani Choudhary; Shoumyo Bhattacharya; Varun Bhardwaj; Sumit Singla; Alex Joseph
Journal:  Eur J Med Chem       Date:  2014-04-15       Impact factor: 6.514

6.  Synthesis of variously coupled conjugates of D-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase.

Authors:  Sándor Kun; Gergo Z Nagy; Marietta Tóth; Laura Czecze; Albert Nguyen Van Nhien; Tibor Docsa; Pál Gergely; Maria-Despoina Charavgi; Paraskevi V Skourti; Evangelia D Chrysina; Tamás Patonay; László Somsák
Journal:  Carbohydr Res       Date:  2011-03-08       Impact factor: 2.104

7.  2-Alkylamino- and alkoxy-substituted 2-amino-1,3,4-oxadiazoles-O-Alkyl benzohydroxamate esters replacements retain the desired inhibition and selectivity against MEK (MAP ERK kinase).

Authors:  Joseph S Warmus; Cathlin Flamme; Lu Yan Zhang; Stephen Barrett; Alexander Bridges; Huifen Chen; Richard Gowan; Michael Kaufman; Judy Sebolt-Leopold; Wilbur Leopold; Ronald Merriman; Jeffrey Ohren; Alexander Pavlovsky; Sally Przybranowski; Haile Tecle; Heather Valik; Christopher Whitehead; Erli Zhang
Journal:  Bioorg Med Chem Lett       Date:  2008-10-07       Impact factor: 2.823

8.  Synthesis and structure-activity relationships of C-glycosylated oxadiazoles as inhibitors of glycogen phosphorylase.

Authors:  Marietta Tóth; Sándor Kun; Eva Bokor; Mahmoud Benltifa; Gaylord Tallec; Sébastien Vidal; Tibor Docsa; Pál Gergely; László Somsák; Jean-Pierre Praly
Journal:  Bioorg Med Chem       Date:  2009-04-23       Impact factor: 3.641

9.  Acceptor Derivatization of the 4CzIPN TADF System: Color Tuning and Introduction of Functional Groups.

Authors:  Fabian Hundemer; Lorenz Graf von Reventlow; Céline Leonhardt; Mika Polamo; Martin Nieger; Stefan M Seifermann; Alexander Colsmann; Stefan Bräse
Journal:  ChemistryOpen       Date:  2019-12-13       Impact factor: 2.911

10.  UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow.

Authors:  Luke Green; Keith Livingstone; Sophie Bertrand; Simon Peace; Craig Jamieson
Journal:  Chemistry       Date:  2020-10-12       Impact factor: 5.236
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  3 in total

Review 1.  Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.

Authors:  Laura Buglioni; Fabian Raymenants; Aidan Slattery; Stefan D A Zondag; Timothy Noël
Journal:  Chem Rev       Date:  2021-08-10       Impact factor: 60.622

2.  Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography.

Authors:  Kian Donnelly; Marcus Baumann
Journal:  Beilstein J Org Chem       Date:  2022-02-25       Impact factor: 2.883

3.  UV-Induced 1,3,4-Oxadiazole Formation from 5-Substituted Tetrazoles and Carboxylic Acids in Flow.

Authors:  Luke Green; Keith Livingstone; Sophie Bertrand; Simon Peace; Craig Jamieson
Journal:  Chemistry       Date:  2020-10-12       Impact factor: 5.236
  3 in total

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