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Literature DB >> 24385679

Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.

Qin Zang¹, Aihua Zhou¹, Salim Javed², Pradip K Maity¹, Chris A Knudtson¹, Danse Bi¹, Jared J Hastings¹, Fatima Z Basha³, Paul R Hanson¹.

Abstract

A novel one-pot sulfonylation/intramolecular thia-Michael protocol is reported for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. Sulfonylation between cysteine ethyl ester/cysteamine and 2-chloroethanesulfonyl chloride, followed by in situ intramolecular thia-Michael addition, was achieved and afforded the titled 1,5,2-dithiazepine-1,1-dioxide scaffolds. Diversification was demonstrated for future library synthesis.

Entities: CellLine Chemical Disease

Year: 2012 PMID： 24385679 PMCID： PMC3873773 DOI： 10.3987/COM-12-S(N)121

Source DB: PubMed Journal: Heterocycles ISSN： 0385-5414 Impact factor: 0.831

32 in total

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Review 4. Recent developments in the field of oxa-Michael reactions.

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5. Stereoselective synthesis of 2,6-cis- and 2,6-trans-piperidines through organocatalytic aza-Michael reactions: a facile synthesis of (+)-myrtine and (-)-epimyrtine.

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6. Application of a Double Aza-Michael Reaction in a 'Click, Click, Cy-Click' Strategy: From Bench to Flow.

Authors: Qin Zang; Salim Javed; Farman Ullah; Aihua Zhou; Christopher A Knudtson; Danse Bi; Fatima Z Basha; Michael G Organ; Paul R Hanson
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7. Tandem asymmetric Michael reaction-intramolecular Michael addition. An easy entry to chiral fluorinated 1,4-dihydropyridines.

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8. Efficient synthesis of multicyclic spirooxindoles via a cascade Michael/Michael/oxa-Michael reaction of curcumins and isatylidene malononitriles.

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