Res Chem Intermed
https://doi.org/10.1007/s11164-017-3217-8
1 3
Et
3
N catalyzed the diastereoselective synthesis
of functionalized cyclohexanones by condensation
of acetoacetanilide and various aldehydes in mild
conditions
Maryam Fatahpour
1
· Nourallah Hazeri
1
· Belgheis Adrom
1
·
Malek Taher Maghsoodlou
1
· Mojtaba Lashkari
2
Received: 4 August 2017 / Accepted: 27 November 2017
© Springer Science+Business Media B.V., part of Springer Nature 2017
Abstract A facile synthetic strategy has been reported for the diastereoselec-
tive synthesis of N,N′-diaryl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-
dicarboxamide via Et
3
N-catalyzed. Acetoacetanilide undergoes a diastereoselec-
tive condensation reaction with various aromatic and aliphatic aldehydes in EtOH
at 50 °C to aford desirable products via one-pot pseudo-three-component reaction.
The present protocol provides an inexpensive and efcient route to obtain function-
alized cyclohexanones containing four quaternary stereogenic centers with high
yields from the simple and readily available starting materials under mild conditions
in shorter reaction times. The products have been characterized by IR,
1
H NMR, and
13
C NMR spectroscopy. The stereoselectivity of compounds was established with
crystallography and NMR spectroscopy.
* Nourallah Hazeri
nhazeri@chem.usb.ac.ir; n_hazeri@yahoo.com
1
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan,
P.O. Box 98135-674, Zahedan, Iran
2
Faculty of Sciences, Velayat University, Iranshahr, Iran