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

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dc.contributor.author

Lipińska, Teodozja M.

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dc.contributor.author

Piechocka, Katarzyna

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Denisiuk, Monika

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Chmiel, Beata

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dc.contributor.author

Skórska-Stania, Agnieszka [SAP12019197]

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dc.date.accessioned

2015-02-26T08:01:31Z

dc.date.available

2015-02-26T08:01:31Z

dc.date.issued

2012

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dc.identifier.issn

1551-7004

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dc.identifier.uri

http://ruj.uj.edu.pl/xmlui/handle/item/3337

dc.language

eng

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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

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dc.type

JournalArticle

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dc.description.physical

264-280

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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.

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dc.subject.en

Biphasic O - tosylation

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dc.subject.en

cinchonicine

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dc.subject.en

conformational analysis

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dc.subject.en

microwave enhancement

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dc.subject.en

X - ray structure

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dc.description.volume

2012

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dc.description.number

6

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dc.identifier.doi

10.3998/ark.5550190.0013.625

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dc.identifier.eissn

1551-7012

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dc.title.journal

Arkivoc

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dc.language.container

eng

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dc.affiliation

Wydział Chemii : Zakład Krystalochemii i Krystalofizyki

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dc.subtype

Article

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dc.identifier.articleid

12-6864OP

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.pointsMNiSW

[2012 A]: 20



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