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Microwave-assisted Synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines From 4-aminobutanol

Microwave-assisted Synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines From 4-aminobutanol

María C Mollo, Natalia B Kilimciler, Juan A Bisceglia, Liliana R Orelli

Beilstein J Org Chem. 2020 Jan 6;16:32-38.

PMID: 31976014

Abstract:

A general procedure for the synthesis of 2-substituted tetrahydro-1,3-thiazepines by MW-assisted cyclization of 4-thioamidobutanols is presented. The acyclic precursors were prepared in high overall yields by an expeditious three-step diacylation/thionation/deprotection sequence from 4-aminobutanol. Microwave-assisted ring closure of 4-thioamido alcohols promoted by trimethylsilyl polyphosphate (PPSE) in solvent-free conditions allowed for the synthesis of several hitherto unreported seven-membered iminothioethers bearing 2-aryl, alkenyl, aralkyl and alkyl substituents. The cyclodehydration reaction is likely to involve an SN2-type displacement and affords good to excellent yields of the desired heterocycles in very short reaction times.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP40623469	Trimethylsilyl polyphosphate		40623-46-9	Price

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