Home / Publications / Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement

Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement

Alexander Georgievich Badamshin 1, 2
Alexander Georgievich Badamshin
Leonid Vasilevich Spirikhin 2
Leonid Vasilevich Spirikhin
Rinat Faritovich Salikov 3
Rinat Faritovich Salikov
Vladimir Anatol'evich Dokichev 1, 2
Vladimir Anatol'evich Dokichev
Published 2015-11-09
CommunicationVolume 25, Issue 6, 438-439
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Badamshin A. G. et al. Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 438-439.
GOST all authors (up to 50) Copy
Badamshin A. G., Spirikhin L. V., Salikov R. F., Dokichev V. A., Tomilov Y. V. Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement // Mendeleev Communications. 2015. Vol. 25. No. 6. pp. 438-439.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.11.013
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.013
TI - Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement
T2 - Mendeleev Communications
AU - Badamshin, Alexander Georgievich
AU - Spirikhin, Leonid Vasilevich
AU - Salikov, Rinat Faritovich
AU - Dokichev, Vladimir Anatol'evich
AU - Tomilov, Yury Vasil'evich
PY - 2015
DA - 2015/11/09
PB - Mendeleev Communications
SP - 438-439
IS - 6
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Badamshin,
author = {Alexander Georgievich Badamshin and Leonid Vasilevich Spirikhin and Rinat Faritovich Salikov and Vladimir Anatol'evich Dokichev and Yury Vasil'evich Tomilov},
title = {Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.013},
number = {6},
pages = {438--439},
doi = {10.1016/j.mencom.2015.11.013}
}
MLA
Cite this
MLA Copy
Badamshin, Alexander Georgievich, et al. “Lewis acid-catalyzed reactions of N-allylanilines with diazo compounds involving aza-Claisen rearrangement.” Mendeleev Communications, vol. 25, no. 6, Nov. 2015, pp. 438-439. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.11.013.

Abstract

N-Allyl-N-methylanilines react with methyl diazoacetate or diazoacetone in the presence of Y, Sc or Sm triflates to give the corresponding methyl N-(2-allylaryl)-N-methylglycinates or 2-allyl-N-methyl-N-(2-oxopropyl)aniline. The formation of these compounds involves the aza-Claisen rearrangement.

References

2.
Catalytic decomposition of diazomethane as a general method for the methylenation of chemical compounds
Tomilov Y.V., Dokitchev V.A., Dzhemilev U.M., Nefedov O.M.
Russian Chemical Reviews, 1993
3.
O. M. Nefedov, E.A. Shapiro and A. B. Dyatkin, in Supplement B: The Chemistry of Acid Derivatives, ed. S. Patai, Wiley, New York, 1992, ch. 25
4.
10.1016/j.mencom.2015.11.013_bib0020
Zollinger
Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds, 1995
5.
10.1016/j.mencom.2015.11.013_bib0025
Doyle
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, 1998
6.
10.1016/j.mencom.2015.11.013_bib0030
Zhou
Synlett, 2010
9.
Reactions of diazo esters with electron-deficient alkenes in the presence of Lewis acids
Novikov R.A., Platonov D.N., Dokichev V.A., Tomilov Y.V., Nefedov O.M.
Russian Chemical Bulletin, 2010
10.
10.1016/j.mencom.2015.11.013_sbref0050a
Nubbemeyer
2007
11.
Recent Advances in Charge-Accelerated Aza-Claisen Rearrangements
12.
10.1016/j.mencom.2015.11.013_sbref0050c
Sharma
J. Curr. Chem. Pharm. Sci., 2013
14.
Microwave-assisted aza-Cope rearrangement of N-allylanilines
González I., Bellas I., Souto A., Rodríguez R., Cruces J.
Tetrahedron Letters, 2008
15.
Deprotection of Allyl Groups with Sulfinic Acids and Palladium Catalyst
Honda M., Morita H., Nagakura I.
Journal of Organic Chemistry, 1997
16.
Metal-Free Reductive Cleavage of CN and SN Bonds by Photoactivated Electron Transfer from a Neutral Organic Donor
O'Sullivan S., Doni E., Tuttle T., Murphy J.A.
Angewandte Chemie - International Edition, 2013
17.
Stevens Rearrangement of Anilinium Salts By the Action Sodium Carbonate Hexahydrate
Shakhbazyan L.G., Babakhanyan A.V., Grigoryan D.V., Kocharyan S.T.
Russian Journal of General Chemistry, 2003
18.
A New Strategy for the Construction of α-Amino Acid Esters via Decarboxylation
Zhang J., Jiang J., Li Y., Zhao Y., Wan X.
Organic Letters, 2013