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Synthesis Of Substituted Indenes And N-Fmoc 2-aminoalkanesulfonyl Chlorides

Posted on:2016-08-29Degree:DoctorType:Dissertation
Country:ChinaCandidate:Haiouani KheiraFull Text:PDF
GTID:1221330473962549Subject:Chemistry
Abstract/Summary:PDF Full Text Request
Tandem reactions have attracted more attention than corresponding multi-step reactions due to their high efficiency and convenience in synthetic organic chemistry. Tandem Friedel-Crafts reactions, if well organized, could simplify many otherwise difficult preparations of substituted arenes. Substituted indenes signify a very important class of carbocyclic compounds with interesting biological activities. They have been widely applied as very useful as ligands in tailored metallocene complexes, particularly for Group four metallocene catalysts for olefin polymerization. Herein, we synthesized a series of indenes derivatives from cinnamaldehydes and arenes via AlCl3-promoted tandem Friedel-Crafts alkylation. The scope and limitation of this tandem alkylation reaction were explored. A plausible reaction mechanism is also discussed. The current method provides a convenient method for the preparation of substituted indenes using a readily available and low cost catalyst and starting materials.N-Protected aminoalkanesulfonyl chlorides are useful and efficient building blocks in the synthesis of sulfonopeptides. Herein, we synthesized a series of Fmoc-protected 2-aminoalkanesulfonyl chlorides with various functionalized side-chains for the synthesis of sulfonopeptides via a radical addition reaction and following oxidative sulfonochlorination with the N-chlorosuccimide (NCS)/HCl. The recent process is a convenient and useful process for the preparation of Fmoc-protected 2-aminoalkanesulfonyl chlorides with different functionalized side-chains in good to excellent yields from simple starting materials...
Keywords/Search Tags:Arene, Cinnamaldehyde, Aluminum chloride, Friedel-Crafts alkylation, Indene, Tandem reaction, Building block, Oxidative sulfonochlorination, Radical reaction, Fmoc, Sulfonyl chloride, Xanthate
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