Microwave-assisted synthesis of 2-substituted 4,5,6,7-tetrahydro-1,3-thiazepines from 4-aminobutanol.
PPSE
cyclodehydration
medium-size heterocycles
microwaves
tetrahydrothiazepines
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2020
2020
Historique:
received:
26
10
2019
accepted:
11
12
2019
entrez:
25
1
2020
pubmed:
25
1
2020
medline:
25
1
2020
Statut:
epublish
Résumé
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 S
Identifiants
pubmed: 31976014
doi: 10.3762/bjoc.16.5
pmc: PMC6964664
doi:
Types de publication
Journal Article
Langues
eng
Pagination
32-38Informations de copyright
Copyright © 2020, Mollo et al.; licensee Beilstein-Institut.
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