Microwave-assisted Synthesis of 2-Substituted 4,5,6,7-Tetrahydro-1,3-thiazepines from 4-Aminobutanol
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A general procedure for the synthesis of 2-substituted tetrahydro-1,3-thiazepines is presented, by MW-assisted cyclization of 4-thioamidobutanols. 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-thioamidoalcohols 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 a SN2-type displacement and affords good to excellent yields of the desired heterocycles in very short reaction times.
2016 ◽
Vol 12
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pp. 2026-2031
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2005 ◽
Vol 2005
(1)
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pp. 27-28
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2011 ◽
Vol 22
(12)
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pp. 2396-2402
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2021 ◽
2001 ◽
Vol 42
(46)
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pp. 8211-8213
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