Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Oxygenative cleavage of an inert C Ar –NH 2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C–N bond cleavage are incorporated into the ta...

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Veröffentlicht in:	Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (7), p.1735-1742
Hauptverfasser:	Botla, Vinayak, Pilli, NavyaSree, Malapaka, Chandrasekharam
Format:	Artikel
Sprache:	eng
Schlagworte:	Aminoquinolines Bioactive compounds Catalysis Chemical reactions Cleavage Coupling (molecular) Crystallography Derivatives Green chemistry Migration Optimization
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creator	Botla, Vinayak Pilli, NavyaSree Malapaka, Chandrasekharam
description	Oxygenative cleavage of an inert C Ar –NH 2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C–N bond cleavage are incorporated into the target molecule and is effected without the need for N -oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.
doi_str_mv	10.1039/C9GC00289H
format	Article
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The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.</description><subject>Aminoquinolines</subject><subject>Bioactive compounds</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>Coupling (molecular)</subject><subject>Crystallography</subject><subject>Derivatives</subject><subject>Green chemistry</subject><subject>Migration</subject><subject>Optimization</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpFkM1OAyEUhYnRxFrd-AQk7kxHgWFgWJqJtiaNbux6wjDQ0rRQgbbWjb6Db-iTOFqjm_uXc797cwA4x-gKo1xcV2JYIURKMToAPUxZngnC0eFfzcgxOIlxjhDGnNEeeJs4JZNc7F51O4Dewa1MOkD_sptqJ5PdaKgWWm7kVENvoHU6JFh9vn88wMa7Fm5tmkHlnfJLm6RLsBzwTC6t8zDOrEndBiz3g-d1FxYdAbY62M0PPJ6CIyMXUZ_95j6Y3N0-VaNs_Di8r27GmSKCpUwTyUqpGCLCUKaMpJS3ohCFNqLNadlQ3jUyx5w3nLRFwQVRsqHatIQwZPI-uNhzV6F7RMdUz_06uO5kTQhCpcAFzzvV5V6lgo8xaFOvgl3KsKsxqr8Nrv8Nzr8AMflvXA</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Botla, Vinayak</creator><creator>Pilli, NavyaSree</creator><creator>Malapaka, Chandrasekharam</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-5413-0650</orcidid></search><sort><creationdate>2019</creationdate><title>Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives</title><author>Botla, Vinayak ; Pilli, NavyaSree ; Malapaka, Chandrasekharam</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-e2a68ac6029f46cfa447d9595ef9d348b47595a3177b72d55792cab4efd2260f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aminoquinolines</topic><topic>Bioactive compounds</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>Coupling (molecular)</topic><topic>Crystallography</topic><topic>Derivatives</topic><topic>Green chemistry</topic><topic>Migration</topic><topic>Optimization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Botla, Vinayak</creatorcontrib><creatorcontrib>Pilli, NavyaSree</creatorcontrib><creatorcontrib>Malapaka, Chandrasekharam</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Botla, Vinayak</au><au>Pilli, NavyaSree</au><au>Malapaka, Chandrasekharam</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2019</date><risdate>2019</risdate><volume>21</volume><issue>7</issue><spage>1735</spage><epage>1742</epage><pages>1735-1742</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>Oxygenative cleavage of an inert C Ar –NH 2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C–N bond cleavage are incorporated into the target molecule and is effected without the need for N -oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/C9GC00289H</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-5413-0650</orcidid></addata></record>
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source	Royal Society Of Chemistry Journals; Alma/SFX Local Collection
subjects	Aminoquinolines Bioactive compounds Catalysis Chemical reactions Cleavage Coupling (molecular) Crystallography Derivatives Green chemistry Migration Optimization
title	Uncatalyzed, on water oxygenative cleavage of inert C–N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives
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