Probing the mechanism of the Ugi four-component reaction with charge-tagged reagents by ESI-MS(/MS)

The mechanism of the Ugi four-component reaction has been investigated by electrospray ionization (tandem) mass spectrometry using charge-tagged reagents (a carboxylic acid or an amine) to favour detection. Key intermediates were transferred directly via ESI(+) from the reaction solution to the gas...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 50; no. 3; pp. 338 - 340
Main Authors Medeiros, Gisele A, da Silva, Wender A, Bataglion, Giovana A, Ferreira, Davi A C, de Oliveira, Heibbe C B, Eberlin, Marcos N, Neto, Brenno A D
Format Journal Article
LanguageEnglish
Published England 11.01.2014
Subjects
Amines - chemistry
Carboxylic acids
Carboxylic Acids - chemistry
Gases - chemistry
Spectrometry, Mass, Electrospray Ionization
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Summary:The mechanism of the Ugi four-component reaction has been investigated by electrospray ionization (tandem) mass spectrometry using charge-tagged reagents (a carboxylic acid or an amine) to favour detection. Key intermediates were transferred directly via ESI(+) from the reaction solution to the gas phase and characterized by MS measurements and MS/MS collision induced dissociation. The Mumm rearrangement (final step) was also investigated by both travelling wave ion mobility mass spectrometry and DFT calculations. The data seem to consolidate the amazingly selective mechanism of this intricate four-component reaction.
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ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc47156j