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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
Journal
Arkivoc
Author
Lipińska Teodozja M.
Piechocka Katarzyna
Denisiuk Monika
Chmiel Beata
Skórska-Stania Agnieszka
Volume
2012
Number
6
Pages
264-280
Article ID
12-6864OP
ISSN
1551-7004
eISSN
1551-7012
Keywords in English
Biphasic O - tosylation
cinchonicine
conformational analysis
microwave enhancement
X - ray structure
Access date
2019-01-17
Language
English
Journal language
English
Abstract in English
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.
Affiliation
Wydział Chemii : Zakład Krystalochemii i Krystalofizyki
Scopus© citations
2
| cris.lastimport.wos | 2024-04-09T23:07:47Z | |
| 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.affiliation | Wydział Chemii : Zakład Krystalochemii i Krystalofizyki | pl |
| 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 - 131911 | pl |
| dc.date.accession | 2019-01-17 | pl |
| dc.date.accessioned | 2015-02-26T08:01:31Z | |
| dc.date.available | 2015-02-26T08:01:31Z | |
| dc.date.issued | 2012 | pl |
| dc.date.openaccess | 0 | |
| dc.description.accesstime | w momencie opublikowania | |
| dc.description.number | 6 | pl |
| dc.description.physical | 264-280 | pl |
| dc.description.version | ostateczna wersja wydawcy | |
| dc.description.volume | 2012 | pl |
| dc.identifier.articleid | 12-6864OP | pl |
| dc.identifier.doi | 10.3998/ark.5550190.0013.625 | pl |
| dc.identifier.eissn | 1551-7012 | pl |
| dc.identifier.issn | 1551-7004 | pl |
| dc.identifier.project | ROD UJ / P | pl |
| dc.identifier.uri | http://ruj.uj.edu.pl/xmlui/handle/item/3337 | |
| dc.identifier.weblink | https://quod.lib.umich.edu/a/ark/5550190.0013.625/1 | pl |
| dc.language | eng | pl |
| dc.language.container | eng | pl |
| dc.rights | Udzielam licencji. Uznanie autorstwa - Użycie niekomercyjne 3.0 | * |
| dc.rights.licence | CC-BY-NC | |
| dc.rights.uri | http://creativecommons.org/licenses/by-nc/3.0/legalcode | * |
| dc.share.type | otwarte czasopismo | |
| 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.subtype | Article | 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.title.journal | Arkivoc | pl |
| dc.type | JournalArticle | pl |
| dspace.entity.type | Publication |
cris.lastimport.wos
2024-04-09T23:07:47Z dc.abstract.enpl
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. dc.affiliationpl
Wydział Chemii : Zakład Krystalochemii i Krystalofizyki dc.contributor.authorpl
Lipińska, Teodozja M. dc.contributor.authorpl
Piechocka, Katarzyna dc.contributor.authorpl
Denisiuk, Monika dc.contributor.authorpl
Chmiel, Beata dc.contributor.authorpl
Skórska-Stania, Agnieszka - 131911 dc.date.accessionpl
2019-01-17 dc.date.accessioned
2015-02-26T08:01:31Z dc.date.available
2015-02-26T08:01:31Z dc.date.issuedpl
2012 dc.date.openaccess
0 dc.description.accesstime
w momencie opublikowania dc.description.numberpl
6 dc.description.physicalpl
264-280 dc.description.version
ostateczna wersja wydawcy dc.description.volumepl
2012 dc.identifier.articleidpl
12-6864OP dc.identifier.doipl
10.3998/ark.5550190.0013.625 dc.identifier.eissnpl
1551-7012 dc.identifier.issnpl
1551-7004 dc.identifier.projectpl
ROD UJ / P dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/3337 dc.identifier.weblinkpl
https://quod.lib.umich.edu/a/ark/5550190.0013.625/1 dc.languagepl
eng dc.language.containerpl
eng dc.rights*
Udzielam licencji. Uznanie autorstwa - Użycie niekomercyjne 3.0 dc.rights.licence
CC-BY-NC dc.rights.uri*
http://creativecommons.org/licenses/by-nc/3.0/legalcode dc.share.type
otwarte czasopismo dc.subject.enpl
Biphasic O - tosylation dc.subject.enpl
cinchonicine dc.subject.enpl
conformational analysis dc.subject.enpl
microwave enhancement dc.subject.enpl
X - ray structure dc.subtypepl
Article dc.titlepl
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 dc.title.journalpl
Arkivoc dc.typepl
JournalArticle dspace.entity.type
Publication Affiliations
No affiliation
Lipińska, Teodozja M.
Piechocka, Katarzyna
Denisiuk, Monika
Chmiel, Beata
Skórska-Stania, Agnieszka
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