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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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2014-01, Vol.5 (3), p.338-34 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | 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 |
| description | 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.
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. |
| doi_str_mv | 10.1039/c3cc47156j |
| format | Article |
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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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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.
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.</description><subject>Amines - chemistry</subject><subject>Carboxylic acids</subject><subject>Carboxylic Acids - chemistry</subject><subject>Gases - chemistry</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0c9LwzAUB_AgipvTi3clxynUNb_a9Chl6mRDYQ68lSRNu461mUmH7L83--G8mkvCex8evG8AuEbhAwpJMlBEKRojFi1OQBeRiAaM8s_T7ZslQUwo64AL5xahP4jxc9DBFFOaUNQF6t0aWTUlbOca1lrNRVO5GppiV5iVFSzM2gbK1CvT6KaFVgvVVqaB31U7h97bUgetKEudb3ulNw7KDRxOR8Fk2h9MpneX4KwQS6evDncPzJ6GH-lLMH57HqWP40ARituAYpkIKuM41ohJmRdS4pwXUiCdS8wFiRKVJ0zynNOQKaV4HBZRQnikOQoxJj3Q389dWfO11q7N6sopvVyKRpu1y5BfmbDQr_4PGlGeUIqZp_d7qqxxzuoiW9mqFnaToTDb5p-lJE13-b96fHuYu5a1zo_0N3APbvbAOnXs_n0g-QHnP4kt</recordid><startdate>20140111</startdate><enddate>20140111</enddate><creator>Medeiros, Gisele A</creator><creator>da Silva, Wender A</creator><creator>Bataglion, Giovana A</creator><creator>Ferreira, Davi A. C</creator><creator>de Oliveira, Heibbe C. B</creator><creator>Eberlin, Marcos N</creator><creator>Neto, Brenno A. D</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20140111</creationdate><title>Probing the mechanism of the Ugi four-component reaction with charge-tagged reagents by ESI-MS(/MS)</title><author>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</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c342t-42b9a4b777e15bbdfbb2d8fba1edb28a369cd95b8d8405ccc870f69386e810223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Amines - chemistry</topic><topic>Carboxylic acids</topic><topic>Carboxylic Acids - chemistry</topic><topic>Gases - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Medeiros, Gisele A</creatorcontrib><creatorcontrib>da Silva, Wender A</creatorcontrib><creatorcontrib>Bataglion, Giovana A</creatorcontrib><creatorcontrib>Ferreira, Davi A. C</creatorcontrib><creatorcontrib>de Oliveira, Heibbe C. B</creatorcontrib><creatorcontrib>Eberlin, Marcos N</creatorcontrib><creatorcontrib>Neto, Brenno A. D</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Medeiros, Gisele A</au><au>da Silva, Wender A</au><au>Bataglion, Giovana A</au><au>Ferreira, Davi A. C</au><au>de Oliveira, Heibbe C. B</au><au>Eberlin, Marcos N</au><au>Neto, Brenno A. D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Probing the mechanism of the Ugi four-component reaction with charge-tagged reagents by ESI-MS(/MS)</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2014-01-11</date><risdate>2014</risdate><volume>5</volume><issue>3</issue><spage>338</spage><epage>34</epage><pages>338-34</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>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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| fulltext | fulltext |
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| ispartof | Chemical communications (Cambridge, England), 2014-01, Vol.5 (3), p.338-34 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines - chemistry Carboxylic acids Carboxylic Acids - chemistry Gases - chemistry Spectrometry, Mass, Electrospray Ionization |
| title | Probing the mechanism of the Ugi four-component reaction with charge-tagged reagents by ESI-MS(/MS) |
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