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Journal ArticleDOI

Application of Microwave Irradiation Techniques for the Syntheses of Cinnamic Acids by Doebner Condensation

01 Feb 1999-Synthetic Communications (Taylor & Francis Group)-Vol. 29, Iss: 4, pp 573-581
TL;DR: The reaction rate of Doebner condensation to achieve cinnamic acids can be dramatically enhanced by irradiating the reaction mixture containing an aromatic aldehyde, malonic acid, pyridine and a trace of piperidine with a commercial microwave oven as discussed by the authors.
About: This article is published in Synthetic Communications.The article was published on 1999-02-01. It has received 30 citations till now. The article focuses on the topics: Malonic acid & Aldehyde.
Citations
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Journal ArticleDOI
TL;DR: In this paper, the classical Knoevenagel-Doebner reaction is reinvestigated where the direct synthesis of substituted 4-vinylphenols instead of the expected 4-hydroxycinnamic acids is described.

69 citations

Journal ArticleDOI
TL;DR: A Thai basil variety accumulating relatively large amounts of the simplest volatile allylphenol, methylchavicol, is subjected to in vivo administration of radiolabeled precursors and assays of protein preparations in vitro, and the biosynthesis of chavicol was shown to occur via the phenylpropanoid pathway to p-coumaryl alcohol.
Abstract: Propenyl- and allyl-phenols, such as methylchavicol, p-anol and eugenol, have gained importance as flavoring agents and also as putative precursors in the biosynthesis of 9,9′-deoxygenated lignans, many of which have potential medicinal applications. In spite of several decades of investigation, however, the complete biosynthetic pathway to a propenyl/allylphenol had not yet been reported. We have subjected a Thai basil variety accumulating relatively large amounts of the simplest volatile allylphenol, methylchavicol, to in vivo administration of radiolabeled precursors and assays of protein preparations in vitro. Through these experiments, the biosynthesis of chavicol was shown to occur via the phenylpropanoid pathway to p-coumaryl alcohol. Various possibilities leading to deoxygenation of the latter were examined, including reduction of the side-chain double bond to form p-dihydrocoumaryl alcohol, followed by dehydration to afford chavicol, as well as formation of p-methoxycinnamyl alcohol, with further side-chain modification to afford methylchavicol. A third possibility studied was activation of the side-chain alcohol of p-coumaryl alcohol, e.g.via esterification, to form a more facile leaving group via reductive elimination. The latter was shown to be the case using p-coumaryl esters as potential substrates for a NAD(P)H-dependent reductase to afford chavicol, which is then O-methylated to afford methylchavicol.

68 citations

Journal ArticleDOI
TL;DR: In this article, the multicomponent reactions of 3-amino-1,2,4-triazoles/5-aminotetrazole with phenylpyruvic acids and aromatic aldehydes were studied using conventional thermal heating, ultrasonification and microwave dielectric heating.

51 citations

Journal ArticleDOI
TL;DR: This method provides a new avenue for the synthesis of vinyl sulfones via a decarboxylative radical coupling strategy by employing a catalytic amount of Cu(ClO4)2·6H2O, TBHP in decane as an oxidant, and 1,10-phenanthroline as a ligand.
Abstract: Copper-catalyzed, ligand-promoted decarboxylative coupling of readily available α,β-unsaturated acids with sodium aryl sulfinates is presented. This method provides a new avenue for the synthesis of vinyl sulfones via a decarboxylative radical coupling strategy by employing a catalytic amount of Cu(ClO4)2·6H2O, TBHP in decane as an oxidant, and 1,10-phenanthroline as a ligand. The salient feature of this method is that it furnishes exclusively the (E)-isomer.

49 citations

References
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Book
01 Jan 2003
TL;DR: In this paper, the authors present a method for the synthesis of organic compounds using Spectroscopic methods and Spectral Spectral Methods (SSTM) with a focus on alicyclic and aliphatic compounds.
Abstract: 1. Organic synthesis 2. Experimental techniques. 3. Spectroscopic methods. 4. Solvents and reagents. 5. Aliphatic compounds. 6. Aromatic compounds. 7. Selected alicyclic compounds. 8. Selected heterocyclic compounds. 9. Investigation and characterisation of organic compounds. 10. Physical constants of organic compounds.

6,578 citations

Journal ArticleDOI

1,321 citations

Journal ArticleDOI
TL;DR: In this article, commercial microwave ovens have been safely used to dramatically reduce the reaction times (at comparable yield) of Diels-Alder, Claisen, and ene reactions.

1,028 citations

Book
01 Jan 1982
TL;DR: In each entry, the data provided in each entry includes (where appropriate): Molecular Formula Structure Diagram Preferred names and synonyms CAS Registry Number Physical description Biological Source Stability Solvent of recrystallization Solubility Melting Point/freezing point Boiling Point Density Refractive Index Optical Rotation Use or Importance (including an indication of important reactions) Hazardous and toxic properties selected literature references as discussed by the authors.
Abstract: Data provided in each entry includes (where appropriate): Molecular Formula Structure Diagram Preferred names and synonyms CAS Registry Number Physical description Biological Source Stability Solvent of recrystallization Solubility Melting Point/freezing point Boiling Point Density Refractive Index Optical Rotation Use or Importance (including an indication of important reactions) Hazardous and toxic properties selected literature references.

254 citations

Book
01 Jan 1972

225 citations