An efficient route for the synthesis of 2-arylthiazino[5,6-b]indole derivatives

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Substituted 2-thiobenzamidomethylindole derivatives (14a-e) were prepared by the reaction of 2-aminomethylindole (9) with substituted benzoyl chlorides, followed by sulfurization using Lawesson's reagent. Alternatively, these thioamides were obtained from the amine in one step in an efficient manner by using substituted benzaldehydes in the presence of sulfur, or at room temperature with the aid of substituted methyl dithiobenzoates. The Hugerschoff reactions of thiobenzamides (14a-e) with phenyltrimethylammonium tribromide provided the rare title 2-arylthiazino[5,6-b]indoles (15a-e) in good yields. A convenient one-pot approach for the synthesis of 2-phenyl-1,3-thiazino[5,6-b]indole (15a) from 2-aminomethylindole (9) is also described.

Original languageEnglish
Pages (from-to)4983-4989
Number of pages7
JournalTetrahedron
Volume63
Issue number23
DOIs
Publication statusPublished - Jun 4 2007

Fingerprint

2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Benzaldehydes
Thioamides
Indoles
Sulfur
Amines
Derivatives
Temperature
phenyltrimethylammonium
indole
benzoyl chloride
thiobenzamide

Keywords

  • 2-Aminomethylindole
  • Hugerschoff reaction
  • Thiazino[5,6-b]indole
  • Thioamide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

An efficient route for the synthesis of 2-arylthiazino[5,6-b]indole derivatives. / Csomós, P.; Fodor, L.; Mándity, I.; Bernáth, G.

In: Tetrahedron, Vol. 63, No. 23, 04.06.2007, p. 4983-4989.

Research output: Contribution to journalArticle

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AU - Csomós, P.

AU - Fodor, L.

AU - Mándity, I.

AU - Bernáth, G.

PY - 2007/6/4

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N2 - Substituted 2-thiobenzamidomethylindole derivatives (14a-e) were prepared by the reaction of 2-aminomethylindole (9) with substituted benzoyl chlorides, followed by sulfurization using Lawesson's reagent. Alternatively, these thioamides were obtained from the amine in one step in an efficient manner by using substituted benzaldehydes in the presence of sulfur, or at room temperature with the aid of substituted methyl dithiobenzoates. The Hugerschoff reactions of thiobenzamides (14a-e) with phenyltrimethylammonium tribromide provided the rare title 2-arylthiazino[5,6-b]indoles (15a-e) in good yields. A convenient one-pot approach for the synthesis of 2-phenyl-1,3-thiazino[5,6-b]indole (15a) from 2-aminomethylindole (9) is also described.

AB - Substituted 2-thiobenzamidomethylindole derivatives (14a-e) were prepared by the reaction of 2-aminomethylindole (9) with substituted benzoyl chlorides, followed by sulfurization using Lawesson's reagent. Alternatively, these thioamides were obtained from the amine in one step in an efficient manner by using substituted benzaldehydes in the presence of sulfur, or at room temperature with the aid of substituted methyl dithiobenzoates. The Hugerschoff reactions of thiobenzamides (14a-e) with phenyltrimethylammonium tribromide provided the rare title 2-arylthiazino[5,6-b]indoles (15a-e) in good yields. A convenient one-pot approach for the synthesis of 2-phenyl-1,3-thiazino[5,6-b]indole (15a) from 2-aminomethylindole (9) is also described.

KW - 2-Aminomethylindole

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