Literature DB >> 12967297

New entry to a three-component pyrimidine synthesis by TMS-Ynones via Sonogashira coupling.

Alexei S Karpov1, Thomas J J Müller.   

Abstract

[reaction: see text] TMS-ynones are versatile synthetic equivalents of beta-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides and (TMS)-acetylene with only one equiv (!) of triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition-cyclocondensation sequence.

Entities:  

Year:  2003        PMID: 12967297     DOI: 10.1021/ol035212q

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


  12 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.  Three-component synthesis of benzo[b][1,5]thiazepines via coupling-addition-cyclocondensation sequence.

Authors:  Benjamin Willy; Thomas J J Müller
Journal:  Mol Divers       Date:  2010-02-16       Impact factor: 2.943

3.  One-pot three-step synthesis of 1,2,3-triazoles by copper-catalyzed cycloaddition of azides with alkynes formed by a Sonogashira cross-coupling and desilylation.

Authors:  Frédéric Friscourt; Geert-Jan Boons
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

4.  Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile.

Authors:  Anton A Muravev; Svetlana E Solovieva; Farida B Galieva; Olga B Bazanova; Ildar Kh Rizvanov; Kamil A Ivshin; Olga N Kataeva; Susan E Matthews; Igor S Antipin
Journal:  RSC Adv       Date:  2018-09-21       Impact factor: 3.361

5.  Broad Spectrum Enolate Equivalent for Catalytic Chemo-, Diastereo-, and Enantioselective Addition to N-Boc Imines.

Authors:  Barry M Trost; Chao-I Joey Hung
Journal:  J Am Chem Soc       Date:  2015-12-14       Impact factor: 15.419

6.  Condensation reactions of guanidines with bis-electrophiles: Formation of highly nitrogenous heterocycles.

Authors:  David M Arnold; Matthew G Laporte; Shelby M Anderson; Peter Wipf
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

7.  Consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles with propynal diethylacetal as a three-carbon building block.

Authors:  Lucilla Levi; Christina Boersch; Charlotte F Gers; Eugen Merkul; Thomas J J Müller
Journal:  Molecules       Date:  2011-11-07       Impact factor: 4.411

8.  Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition-cyclocondensation sequences.

Authors:  Natascha Breuer; Irina Gruber; Christoph Janiak; Thomas J J Müller
Journal:  Beilstein J Org Chem       Date:  2019-11-12       Impact factor: 2.883

9.  One-pot three-component synthesis and photophysical characteristics of novel triene merocyanines.

Authors:  Christian Muschelknautz; Robin Visse; Jan Nordmann; Thomas J J Müller
Journal:  Beilstein J Org Chem       Date:  2014-03-05       Impact factor: 2.883

10.  Naturally Inspired Pyrimidines Analogues for Alzheimer's Disease.

Authors:  Shivani Singh; Meenakshi Dhanawat; Sumeet Gupta; Deepak Kumar; Saloni Kakkar; Anroop Nair; Inderjeet Verma; Prerna Sharma
Journal:  Curr Neuropharmacol       Date:  2021       Impact factor: 7.363

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