An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles
Publication type: Journal Article
Publication date: 2005-04-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
1-Benzenesulfonyl-5-aminoindole 5, prepared from 5-nitroindole 3, was condensed with alkyl isothiocyanates and separately with carbon disulfide and alkyl bromides/iodides to furnish efficiently the corresponding N-alkyl-thioureidoindoles 6a–c and the alkyl N-(indol-5′-yl)dithiocarbamates 9a–e, respectively. Their cyclisation using N-bromosuccinimide (NBS) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), in the cold, followed by indolic N-deprotection, furnished regioselectively the 2-alkylamino- and the 2-alkylthiothiazolo[5,4-e]indoles 8a–c and 11a–e, respectively, in good overall yields.
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Chakrabarty M. et al. An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles // Tetrahedron Letters. 2005. Vol. 46. No. 16. pp. 2865-2868.
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Chakrabarty M., Kundu T., Arima S., HARIGAYA Y. An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles // Tetrahedron Letters. 2005. Vol. 46. No. 16. pp. 2865-2868.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2005.02.125
UR - https://doi.org/10.1016/j.tetlet.2005.02.125
TI - An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles
T2 - Tetrahedron Letters
AU - Chakrabarty, Manas
AU - Kundu, Taraknath
AU - Arima, Shiho
AU - HARIGAYA, Yoshihiro
PY - 2005
DA - 2005/04/01
PB - Elsevier
SP - 2865-2868
IS - 16
VL - 46
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
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@article{2005_Chakrabarty,
author = {Manas Chakrabarty and Taraknath Kundu and Shiho Arima and Yoshihiro HARIGAYA},
title = {An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles},
journal = {Tetrahedron Letters},
year = {2005},
volume = {46},
publisher = {Elsevier},
month = {apr},
url = {https://doi.org/10.1016/j.tetlet.2005.02.125},
number = {16},
pages = {2865--2868},
doi = {10.1016/j.tetlet.2005.02.125}
}
Cite this
MLA
Copy
Chakrabarty, Manas, et al. “An expedient, regioselective synthesis of 2-alkylamino- and 2-alkylthiothiazolo[5,4-e]indoles.” Tetrahedron Letters, vol. 46, no. 16, Apr. 2005, pp. 2865-2868. https://doi.org/10.1016/j.tetlet.2005.02.125.