Synthesis and transformations of 4,5‐dihydro‐1,4‐benzothiazepin‐3(2H)‐one derivatives

János Szabó, L. Fodor, Ágnes Katócs, G. Bernáth, P. Sohár

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Abstract

The attempted cyclization of S‐(3,4‐dimethoxyphenyl)‐N‐(hydroxymethyl)thioglycolamide (6) with phosphoryl chloride gave, instead of the expected benzothiazepinone 7e, (3,4‐dimethoxyphenylthio)acetonitrile (8). The product of ring closure of N‐[[2‐(benzoylthio)‐4,5‐dimethoxyphenyl]methyl]‐2‐chloroacetamide (11) with sodium ethoxide was 4,5‐dihydro‐7,8‐dimethoxy‐1,4‐benzothiazepin‐3(2H)‐one (7e). The latter compound can also be prepared in good yield from ethyl S‐[2‐(aminomethyl)‐4,5‐dimethoxyphenyl]thioglycolate (15) in alkaline solution. The thiophenols 16a, b reacted with α‐halogenocarboxylic esters 17 in the presence of sodium methoxide to furnish the corresponding 4,5‐dihydro‐1,4‐benzothiazepin‐3(2H)‐ones 7a–i in high yields in one step. Several conversions of these benzothiazepinones were effected; 3‐thiones 18a, b, sulfones 19a, b, sulfoxide 20, N‐benzoyl 22a and N‐phenylcarbamoyl 22b derivatives were synthesized. LiAlH4 reduction of 7e gave 2,3,4,5‐tetrahydro‐7,8‐dimethoxy‐1,4‐benzothiazepine (21 a).

Original languageEnglish
Pages (from-to)2904-2913
Number of pages10
JournalChemische Berichte
Volume119
Issue number9
DOIs
Publication statusPublished - 1986

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sulfoxide
Thioglycolates
Sulfones
Cyclization
Methanol
Esters
Derivatives
lithium aluminum hydride
sodium ethoxide
thiophenol
phosphoryl chloride
acetonitrile

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and transformations of 4,5‐dihydro‐1,4‐benzothiazepin‐3(2H)‐one derivatives. / Szabó, János; Fodor, L.; Katócs, Ágnes; Bernáth, G.; Sohár, P.

In: Chemische Berichte, Vol. 119, No. 9, 1986, p. 2904-2913.

Research output: Contribution to journalArticle

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