Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes
Publication type: Journal Article
Publication date: 2019-11-21
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
31747752
Organic Chemistry
Abstract
A Brønsted acid-catalyzed pinacol-type rearrangement pathway is reported here to synthesize various substituted α-(3-indolyl) ketones by employing unprotected indoles and α-hydroxy aldehydes as coupling partners. Utilization of economic and readily available Brønsted acid catalyst and use of simple starting precursors exemplify the economic viability of this method. Under this developed protocol, selective migration of aryl over alkyl or a second aryl group is observed depending upon the migratory aptitude of the substituents. Applicability of this method was further demonstrated by synthesizing highly substituted carbazoles through a simple extension of this method to one-pot cascade annulation strategy.
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Total citations:
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Citations from 2024:
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(31.04%)
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Kundu S., Banerjee A., Maji M. S. Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes // Journal of Organic Chemistry. 2019. Vol. 84. No. 24. pp. 16003-16012.
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Kundu S., Banerjee A., Maji M. S. Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes // Journal of Organic Chemistry. 2019. Vol. 84. No. 24. pp. 16003-16012.
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RIS
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TY - JOUR
DO - 10.1021/acs.joc.9b02474
UR - https://doi.org/10.1021/acs.joc.9b02474
TI - Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes
T2 - Journal of Organic Chemistry
AU - Kundu, Samrat
AU - Banerjee, Ankush
AU - Maji, Modhu Sudan
PY - 2019
DA - 2019/11/21
PB - American Chemical Society (ACS)
SP - 16003-16012
IS - 24
VL - 84
PMID - 31747752
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Kundu,
author = {Samrat Kundu and Ankush Banerjee and Modhu Sudan Maji},
title = {Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes},
journal = {Journal of Organic Chemistry},
year = {2019},
volume = {84},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.9b02474},
number = {24},
pages = {16003--16012},
doi = {10.1021/acs.joc.9b02474}
}
Cite this
MLA
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Kundu, Samrat, et al. “Brønsted Acid-Catalyzed Tandem Pinacol-Type Rearrangement for the Synthesis of α-(3-Indolyl) Ketones by Using α-Hydroxy Aldehydes.” Journal of Organic Chemistry, vol. 84, no. 24, Nov. 2019, pp. 16003-16012. https://doi.org/10.1021/acs.joc.9b02474.