The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-methoxybenzoyl chlorides afforded 3,5-diketoesters which were transformed, by treatment with boron tribromide, into functionalized 2-hydroxychroman-4-ones or chromones. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-nitrobenzoyl chlorides and subsequent reduction of the nitro group afforded functionalized 4-hydroxyquinolines. Their tautomeric equilibrium was studied by NMR spectroscopy and by computational methods.
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Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions.
Org Biomol Chem
May 2009
Institut für Chemie, Universität Rostock, Albert-Einstein-Str., 3a, 18059, Rostock, Germany.
The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-methoxybenzoyl chlorides afforded 3,5-diketoesters which were transformed, by treatment with boron tribromide, into functionalized 2-hydroxychroman-4-ones or chromones. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-nitrobenzoyl chlorides and subsequent reduction of the nitro group afforded functionalized 4-hydroxyquinolines. Their tautomeric equilibrium was studied by NMR spectroscopy and by computational methods.
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Org Biomol Chem
February 2006
Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan.
The expedient synthesis of various 1,4-benzodiazepine-2,5-dione compounds, particularly those having substituents at the C3-, N1- and N4-positions is achieved. The important features in these synthetic strategies include: (i) using the coupling reaction of isatoic anhydride with alpha-amino ester for direct construction of the core structure of 1,4-benzodiazepine-2,5-dione; (ii) using potassium carbonate as the base of choice for selective alkylation at the N1-site, while using lithiated 2-ethylacetanilide as the required base to furnish the N4-alkylation; and (iii) using 2-nitrobenzoyl chloride as a synthetic equivalent of anthranilic acid to facilitate the polyethylene resin-bound liquid-phase combinatorial synthesis. The prepared 1,4-benzodiazepine-2,5-dione compounds are evaluated for endothelin receptor antagonism by a functional assay that measures the inhibitory activity against the change of intramolecular calcium ion concentration induced by endothelin-1.
View Article and Find Full Text PDFEffects of heating rate, temperature and iron catalysis on the thermal behaviour and decomposition of 2-nitrobenzoyl chloride.
J Hazard Mater
March 2006
School of Process Environmental and Materials Engineering, University of Leeds, Leeds LS2 9JT, UK.
Runaway reactions arising from the decomposition of thermally unstable materials are a concern in industry due to the potentially devastating effects that they yield. Studies into the occurrence of thermal runaway incidents have shown the most likely cause to be a result of an inadequate investigation of the process prior to its operation on a large-scale. The chlorination of ortho-nitrated carboxylic acids is an industrially important reaction in the fine and agrochemical industries.
View Article and Find Full Text PDFStudy of condition-dependent decomposition reactions; Part I. The thermal behaviour and decomposition of 2-nitrobenzoyl chloride.
J Hazard Mater
November 2004
Chemical Engineering Department, School of Process Environmental and Materials Engineering, University of Leeds, Leeds LS2 9JT, UK.
The risks associated with batch processing in the manufacture of chemicals and pharmaceuticals via highly exothermic reactions are of special interest due to the possibility of runaway reactions. o-Nitrated benzoyl chlorides are intermediates in the production of agrochemicals and are produced via the reaction of o-nitrated carboxylic acids with thionyl chloride in a solvent mixture. ortho-Nitrated acyl chlorides have exploded violently on attempted distillation on numerous occasions.
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J Org Chem
January 2003
Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.
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