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 - Sep 2011

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2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Indoles
Isomers
Derivatives
Esters
Phenylthiourea
Carboxylic Acids
Silicon Dioxide
Nuclear magnetic resonance spectroscopy
Nuclear magnetic resonance
indole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
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.",
author = "P. Csom{\'o}s and L. Fodor and G. Bern{\'a}th and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2011",
month = "9",
doi = "10.1002/jhet.607",
language = "English",
volume = "48",
pages = "1079--1084",
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T1 - 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

AU - Csomós, P.

AU - Fodor, L.

AU - Bernáth, G.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2011/9

Y1 - 2011/9

N2 - 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.

AB - 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.

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JO - Journal of Heterocyclic Chemistry

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