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A Dynamic Multicomponent Approach for One-Pot Synthesis of 3-Thioisoindolinones
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2013 (English)In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 53, no 1-2, 127-132 p.Article in journal (Refereed) Published
Abstract [en]

A dynamic multicomponent reaction concept has been successfully applied to the syntheses of 3-thioisoindolinones and tricyclic gamma-lactams. The reactions were efficiently designed and operated in the absence of any catalyst under mild reaction conditions, resulting in the convenient variation of substituents on the N- and S-positions of the target products.

Place, publisher, year, edition, pages
2013. Vol. 53, no 1-2, 127-132 p.
Keyword [en]
cyclization, dynamic chemistry, heterocycles, isoindolinone, multicomponent reactions
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-34126DOI: 10.1002/ijch.201200101ISI: 000316506000017Scopus ID: 2-s2.0-84876252158OAI: oai:DiVA.org:kth-34126DiVA: diva2:419259
Funder
Swedish Research CouncilEU, European Research Council, MRTN-CT-2006-035614
Note

QC 20130419. Updated from submitted to published.

Available from: 2011-05-26 Created: 2011-05-26 Last updated: 2017-12-11Bibliographically approved
In thesis
1. Dynamic Systems: Evaluation, Screening and Synthetic Application
Open this publication in new window or tab >>Dynamic Systems: Evaluation, Screening and Synthetic Application
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The research work reported in the thesis deals with the development of dynamic covalent systems and their applications in evaluation and screening of protein-ligands and enzyme inhibitors, as well as in synthetic methodologies. The thesis is divided into four parts as described below.

In part one, synthetic methodologies to access 3-functionalized phthalides and 3-thioisoindolinones using the concept of cascade reactions are demonstrated. Efficient syntheses of the target products are designed and performed in one-pot process under mild reaction conditions.

 In part two, phosphine-catalyzed disulfide metathesis for the generation of dynamic carbohydrate system in aqueous solution is demonstrated. In the presence of biological target (Concanavalin A), the optimal dynamic ligand is successfully identified in situ by the 1H STD-NMR spectroscopy.

In part three, lipase-catalyzed resolutions of dynamic reversible systems using reversible cyanohydrin and hemithioacetal reactions in one-pot processes are demonstrated. The dynamic systems are generated under thermodynamic control in organic solution and subsequently resolved by lipase-mediated resolution under kinetic control. The resolution processes resulted in the lipase-selected substrates with high structural and stereochemical specificities.

In the last part, dynamic fragment-based strategy is presented using β-galactosidase as a model target enzyme. Based on our previous study, the best dynamic inhibitor of β-galactosidase was identified using 1H STD-NMR technique from dynamic hemithioacetal systems. The structure of the dynamic inhibitor is tailored by fragment linking and optimization processes. The designed inhibitor structures are then synthesized and tested for inhibition activities against β-galactosidase. 

 

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 69 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:33
Keyword
constitutional dynamic chemistry; dynamic combinatorial chemistry/ resolution; dynamic fragment-based approach; dynamic kinetic resolution; dynamic reversible systems; 1H STD-NMR; multicomponent reaction; tandem reaction
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-34100 (URN)978-91-7415-986-8 (ISBN)
Public defence
2011-06-07, F3, KTH, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
EU, European Research Council, MRTN-CT-2006-035614
Note
QC 20110526Available from: 2011-05-26 Created: 2011-05-25 Last updated: 2011-05-26Bibliographically approved

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