A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes
Publication type: Journal Article
Publication date: 2019-08-08
scimago Q1
wos Q2
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
31283058
General Chemistry
Catalysis
Organic Chemistry
Abstract
A Brønsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.
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Metrics
35
Total citations:
35
Citations from 2024:
11
(31.43%)
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GOST
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Banerjee A., Maji M. S. A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes // Chemistry - A European Journal. 2019. Vol. 25. No. 49. pp. 11521-11527.
GOST all authors (up to 50)
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Banerjee A., Maji M. S. A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes // Chemistry - A European Journal. 2019. Vol. 25. No. 49. pp. 11521-11527.
Cite this
RIS
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TY - JOUR
DO - 10.1002/chem.201902268
UR - https://doi.org/10.1002/chem.201902268
TI - A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes
T2 - Chemistry - A European Journal
AU - Banerjee, Ankush
AU - Maji, Modhu Sudan
PY - 2019
DA - 2019/08/08
PB - Wiley
SP - 11521-11527
IS - 49
VL - 25
PMID - 31283058
SN - 0947-6539
SN - 1521-3765
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2019_Banerjee,
author = {Ankush Banerjee and Modhu Sudan Maji},
title = {A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes},
journal = {Chemistry - A European Journal},
year = {2019},
volume = {25},
publisher = {Wiley},
month = {aug},
url = {https://doi.org/10.1002/chem.201902268},
number = {49},
pages = {11521--11527},
doi = {10.1002/chem.201902268}
}
Cite this
MLA
Copy
Banerjee, Ankush, and Modhu Sudan Maji. “A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes.” Chemistry - A European Journal, vol. 25, no. 49, Aug. 2019, pp. 11521-11527. https://doi.org/10.1002/chem.201902268.