First ultrasound-mediated one-pot synthesis of N-substituted amides

Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl ca...

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Bibliographic Details
Published inUltrasonics sonochemistry Vol. 16; no. 6; pp. 737 - 742
Main Authors Srivastava, Rajendra M., Neves Filho, Ricardo A.W., da Silva, Cecilia A., Bortoluzzi, Adailton J.
Format Journal Article
LanguageEnglish
Published Kidlington Elsevier B.V 01.08.2009
Elsevier
Subjects
1,2,4-Oxadiazoles
Amides
Amides - chemical synthesis
Amides - chemistry
Carbonates - chemistry
Chemistry
Ethyl chloroformate
Exact sciences and technology
General and physical chemistry
Indicators and Reagents - chemistry
Kinetics
Nitrogen - chemistry
Physical chemistry of induced reactions (with radiations, particles and ultrasonics)
Potassium - chemistry
Ultrasonic chemistry
Ultrasonics
Ultrasound
X-ray crystallography
X-ray crystallography
Amides
1,2,4-Oxadiazoles
Ethyl chloroformate
Ultrasound
Methodology
Sonochemistry
Oxadiazole
Activation
X ray
Crystallography
Crystalline state
Amine
Synthesis
Carboxylic acid
Alkyl
Reagents
Carboxamide
Aryl
Structure
Organic compounds
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Summary:Ultrasound irradiation, an efficient and innocuous technique of reagent activation for synthesizing organic compounds, has been applied with success to transform seven carboxylic acids to fourteen secondary amides in good to excellent yields. The reaction has worked well either with aryl or alkyl carboxylic acids as well as with aromatic or aliphatic amines. This methodology is expeditious and reliable for preparing secondary carboxamides which in many cases are embedded in the C-5 side-chain of 1,2,4-oxadiazoles ( 14, 15, 17– 27). The elemental analyses of new compounds ( 19– 27) in conjunction with the spectral data of all synthesized amides gave an idea about their structures, while the crystallographic data of one of the compounds ( 26) supplied information concerning the configurational behavior of the amidic part and also the conformational aspect of the entire molecule in the crystalline state.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1350-4177
1873-2828
DOI:10.1016/j.ultsonch.2009.04.006