Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles
1
Chemical and Analytical Development, Novartis Institute for Biomedical Research, East Hanover, New Jersey 07936
|
Publication type: Journal Article
Publication date: 2003-02-07
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
12608816
Organic Chemistry
Abstract
DABCO is an extremely active catalyst for the methylation of indoles in conjunction with dimethyl carbonate (DMC). This green chemistry is highly effective and produces N-methylindoles in nearly quantitative yields. The reaction sequence consists of competing alkylation and acylation pathways and involves 1,4-diazabicyclo[2.2.2]octane (DABCO) dually as a nucleophilic catalyst, ultimately resulting in a single product: the N-methylated indole.
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Total citations:
77
Citations from 2025:
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BibTex |
MLA
Cite this
GOST
Copy
Shieh W. et al. Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles // Journal of Organic Chemistry. 2003. Vol. 68. No. 5. pp. 1954-1957.
GOST all authors (up to 50)
Copy
Shieh W., Dell S., Bach A., Repič O., Blacklock T. J. Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles // Journal of Organic Chemistry. 2003. Vol. 68. No. 5. pp. 1954-1957.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/jo0266644
UR - https://doi.org/10.1021/jo0266644
TI - Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles
T2 - Journal of Organic Chemistry
AU - Shieh, Wen-Chung
AU - Dell, Steven
AU - Bach, Andrew
AU - Repič, Oljan
AU - Blacklock, Thomas J.
PY - 2003
DA - 2003/02/07
PB - American Chemical Society (ACS)
SP - 1954-1957
IS - 5
VL - 68
PMID - 12608816
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2003_Shieh,
author = {Wen-Chung Shieh and Steven Dell and Andrew Bach and Oljan Repič and Thomas J. Blacklock},
title = {Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles},
journal = {Journal of Organic Chemistry},
year = {2003},
volume = {68},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/jo0266644},
number = {5},
pages = {1954--1957},
doi = {10.1021/jo0266644}
}
Cite this
MLA
Copy
Shieh, Wen-Chung, et al. “Dual Nucleophilic Catalysis with DABCO for the N-Methylation of Indoles.” Journal of Organic Chemistry, vol. 68, no. 5, Feb. 2003, pp. 1954-1957. https://doi.org/10.1021/jo0266644.