Literature DB >> 24433170

Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones.

Pei-Pei Yeh1, David S B Daniels, David B Cordes, Alexandra M Z Slawin, Andrew D Smith.   

Abstract

A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.

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Year:  2014        PMID： 24433170     DOI： 10.1021/ol403697h

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


  10 in total

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Journal:  Materials (Basel)       Date:  2021-12-27       Impact factor: 3.623

2.  Asymmetric Isothiourea-Catalysed Formal [3+2] Cycloadditions of Ammonium Enolates with Oxaziridines.

Authors:  Siobhan R Smith; Charlene Fallan; James E Taylor; Ross McLennan; David S B Daniels; Louis C Morrill; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chemistry       Date:  2015-06-12       Impact factor: 5.236

3.  Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans.

Authors:  Dorine Belmessieri; Alix de la Houpliere; Ewen D D Calder; James E Taylor; Andrew D Smith
Journal:  Chemistry       Date:  2014-07-02       Impact factor: 5.236

4.  Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction.

Authors:  Qijian Ni; Xiaoxiao Song; Jiawen Xiong; Gerhard Raabe; Dieter Enders
Journal:  Chem Commun (Camb)       Date:  2015-01-25       Impact factor: 6.222

Review 5.  Recent advances in the synthesis of 2-pyrones.

Authors:  Jong Seok Lee
Journal:  Mar Drugs       Date:  2015-03-23       Impact factor: 5.118

6.  Enantioselective Synthesis of 3,5,6-Substituted Dihydropyranones and Dihydropyridinones using Isothiourea-Mediated Catalysis.

Authors:  Daniel G Stark; Louis C Morrill; David B Cordes; Alexandra M Z Slawin; Timothy J C O'Riordan; Andrew D Smith
Journal:  Chem Asian J       Date:  2015-11-12

7.  Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies.

Authors:  Daniel G Stark; Patrick Williamson; Emma R Gayner; Stefania F Musolino; Ryan W F Kerr; James E Taylor; Alexandra M Z Slawin; Timothy J C O'Riordan; Stuart A Macgregor; Andrew D Smith
Journal:  Org Biomol Chem       Date:  2016-08-04       Impact factor: 3.876

8.  Crystal structure, Hirshfeld surface analysis and DFT calculations of (E)-3-[1-(2-hy-droxy-phenyl-anilino)ethyl-idene]-6-methyl-pyran-2,4-dione.

Authors:  Imane Faraj; Ali Oubella; Karim Chkirate; Khalil Al Mamari; Tuncer Hökelek; Joel T Mague; Lhoussaine El Ghayati; Nada Kheira Sebbar; El Mokhtar Essassi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2022-07-29

Review 9.  Biosynthesis of α-pyrones.

Authors:  Till F Schäberle
Journal:  Beilstein J Org Chem       Date:  2016-03-24       Impact factor: 2.883

10.  S,O-Ligand-Promoted Palladium-Catalyzed C-H Functionalization Reactions of Nondirected Arenes.

Authors:  Kananat Naksomboon; Carolina Valderas; Melania Gómez-Martínez; Yolanda Álvarez-Casao; M Ángeles Fernández-Ibáñez
Journal:  ACS Catal       Date:  2017-08-18       Impact factor: 13.084
  10 in total

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