Repozytorium Uniwersytetu Jagiellońskiego

Structure-reactivity study of O-tosyl Cinchona alkaloids in their new synthesis and in hydrolysis to 9-epibases : unexpected formation of cinchonicine enol tosylate accelerated by microwave activation

Structure-reactivity study of O-tosyl Cinchona ...

Metadane (Dublin Core)

dc.contributor.author Lipińska, Teodozja M. pl
dc.contributor.author Piechocka, Katarzyna pl
dc.contributor.author Denisiuk, Monika pl
dc.contributor.author Chmiel, Beata pl
dc.contributor.author Skórska-Stania, Agnieszka [SAP12019197] pl
dc.date.accessioned 2015-02-26T08:01:31Z
dc.date.available 2015-02-26T08:01:31Z
dc.date.issued 2012 pl
dc.identifier.issn 1551-7004 pl
dc.identifier.uri http://ruj.uj.edu.pl/xmlui/handle/item/3337
dc.language eng pl
dc.title Structure-reactivity study of O-tosyl Cinchona alkaloids in their new synthesis and in hydrolysis to 9-epibases : unexpected formation of cinchonicine enol tosylate accelerated by microwave activation pl
dc.type JournalArticle pl
dc.description.physical 264-280 pl
dc.abstract.en New methods for O - tosylation of the natural Cinchona alkaloids have been discovered as a biphasic processes with Bu 3 N as a catalyst. The optimized excess of tosy l chloride , necessary for transformation of each of the four alkaloid s into O - tosy l derivative , decreases in the following order : quinine, quinidine, cinchonidine and cinchonine . The same decreasing order has been noticed for the hy drolysis rate of the appropriate tosylates to 9 - epibases . D iffic ult conversion of O - tosy lcinchonine in the hydrolytic medium of aq ueous tarta ric acid gives 9 - epicinchonine together with parallel formation of cinchonicine enol tosylate. The latter product is obtained as the main when both cinchonine and cinchonidine tosylates react in the presence of salicylic acid under controlled microwave heating . On the basis of X - ray structure of the new alkene product, the stereoselective syn - E2 quinuclidine ring opening process , competing to the S N 2 hydrolysis is postulated for this transformation. pl
dc.subject.en Biphasic O - tosylation pl
dc.subject.en cinchonicine pl
dc.subject.en conformational analysis pl
dc.subject.en microwave enhancement pl
dc.subject.en X - ray structure pl
dc.description.volume 2012 pl
dc.description.number 6 pl
dc.identifier.doi 10.3998/ark.5550190.0013.625 pl
dc.identifier.eissn 1551-7012 pl
dc.title.journal Arkivoc pl
dc.language.container eng pl
dc.affiliation Wydział Chemii : Zakład Krystalochemii i Krystalofizyki pl
dc.subtype Article pl
dc.identifier.articleid 12-6864OP pl
dc.rights.original CC-BY-NC; otwarte czasopismo; ostateczna wersja wydawcy; w momencie opublikowania; 0; pl
.pointsMNiSW [2012 A]: 20


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