One-step ring-closure procedure for 4,5-dihydro-1,3-thiazino[5,4-b]indole derivatives with Lawesson's reagent. the fifth dihydro-1,3-thiazino[b]indole isomer

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Abstract

We report a convenient approach for the synthesis of a new ring system: 4,5-dihydro-1,3-thiazino[5,4-b]indoles. The procedure involves the use of Lawesson's reagent in the presence of silica to achieve the one-step ring-closure reactions of 2-benzoylamino-3-hydroxymethylindole intermediates to furnish 4,5-dihydro-2-aryl-1,3-thiazino[5,4-b]indoles. 2-Phenylimino-1,3- thiazino[5,4-b]indoles were obtained via the corresponding 3-phenylthiourea-2- carboxylic acid ester derivatives by chemoselective reduction of the ester group, followed by ring closure under acidic conditions. The structures of the novel products were elucidated by IR, 1H-NMR, and 13C-NMR spectroscopy, including 2D-HMQC, 2D-HMBC, and DEPT measurements.

Original languageEnglish
Pages (from-to)1079-1084
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume48
Issue number5
DOIs
Publication statusPublished - szept. 1 2011

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ASJC Scopus subject areas

  • Organic Chemistry

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