An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides

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Abstract

A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.

Original languageEnglish
Pages (from-to)1475-1480
Number of pages6
JournalTetrahedron
Volume65
Issue number7
DOIs
Publication statusPublished - febr. 14 2009

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Carbolines
Sulfides
Isomerization
Derivatives
indole
trifluoromethanesulfonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{aca481f6164b4dd8a666deef9a1bf7b2,
title = "An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides",
abstract = "A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.",
keywords = "H and C NMR, Bischler-Napieralski reaction, IR, Isomerization, Thiazino[6,5-b]indole, Trifluoromethanesulfonic acid",
author = "P. Csom{\'o}s and L. Fodor and G. Bern{\'a}th and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2009",
month = "2",
day = "14",
doi = "10.1016/j.tet.2008.11.099",
language = "English",
volume = "65",
pages = "1475--1480",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "7",

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TY - JOUR

T1 - An expeditious synthesis for γ-carboline analogue 4-aryl-1,3-thiazino[6,5-b]indole derivatives via the trifluoromethanesulfonic acid-promoted isomerization of 3-amidomethylthioindole intermediates to 2-indolyl sulfides

AU - Csomós, P.

AU - Fodor, L.

AU - Bernáth, G.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2009/2/14

Y1 - 2009/2/14

N2 - A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.

AB - A highly efficient trifluoromethanesulfonic acid-mediated rearrangement of the benzoylaminomethylthio group of 3-benzoylaminomethylthioindoles (7a-e) to position 2 of the indole ring was developed. Thus, 2-benzoylaminomethylthioindoles (9a-e) were obtained in good yields and were involved as key intermediates in the synthesis of the new γ-carboline analogue ring system: 2,9-dihydro-4-aryl-1,3-thiazino[6,5-b]indole derivatives (11a-e). The target thiazinoindoles (11a-e) were prepared via 2-thiobenzoylaminomethylindoles (10a-e) in modified Bischler-Napieralski reactions.

KW - H and C NMR

KW - Bischler-Napieralski reaction

KW - IR

KW - Isomerization

KW - Thiazino[6,5-b]indole

KW - Trifluoromethanesulfonic acid

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U2 - 10.1016/j.tet.2008.11.099

DO - 10.1016/j.tet.2008.11.099

M3 - Article

AN - SCOPUS:58149483480

VL - 65

SP - 1475

EP - 1480

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 7

ER -