Oleylamine-catalyzed Tandem Knoevenagel/Michael Addition of 1,3-Cyclohexanediones with Aromatic Aldehydes

Abstract

A convenient and efficient method was developed for the synthesis of 2,2′-(arylmethylene)bis(3-hydrox- ycyclohex-2-enone) derivatives via the oleylamine-catalyzed tandem Knoevenagel/Michael addition reactions of aromatic aldehydes and cyclohexane-1,3-diones. This transformation proceeded without any metal catalyst in non-toxic solvent at room temperature with high isolated yields. A plausible mechanism for this process was pro-posed.

Keywords

2,2′-(Arylmethylene)bis(3-hydroxycyclohex-2-enone) / Knoevenagel condensation / Michael addition / Oleylamine / Tandem reaction

References

[1] Ren Y, Yang B, Liao X. RSC Adv., 2016, 6: 22034.

[2] Cravotto G, Demetri A, Nano G M, Palmisano G, Penoni A, Tagliapietra S. Eur. J. Org. Chem., 2003, 4438.

[3] Li J T, Li Y W, Song Y L, Chen G F. Ultrason. Sonochem., 2012, 19: 1.

[4] Jung D H, Lee Y R, Kim S H, Lyoo W S. Bull. Korean Chem. Soc., 2009, 30: 1989.

[5] Ilangovan A, Malayappasamy S, Muralidharan S, Maruthamuthu S. Chem. Cent. J., 2011, 5: 81.

[6] Bin L L, Shou J T, Sha H L, Meng L, Na Q, Shuang L T. Eur. J. Chem., 2006, 3: 117.

[7] Nandre K P, Patil V S, Bhosale S V. Chin. Chem. Lett., 2011, 22: 777.

[8] Maghsoodlou M T, Khorassani S M H, Shahkarami Z, Maleki N, Ros-tamizadeh M. Chin. Chem. Lett., 2010, 21: 686.

[9] Rao V K, Kumar M M, Kumar A. Indian J. Chem., 2011, 50B: 1128.

[10] Fan X, Sen L, Zhang Y Z, Hu X Y, Wang X Y, Ji J. Chin. J. Org. Chem., 2005, 25: 1482.

[11] Kantevari S, Bantu R, Nagarapu L. J. Mol. Catal. A: Chem., 2007, 269: 53.

[12] Zhang Y, Sun C, Liang J, Shang Z. Chin. J. Chem., 2010, 28: 2255.

[13] Jiang L, Wang B, Li R R, Shen S, Yu H W, Ye L D. Chin. Chem. Lett., 2014, 25: 1190.

[14] Mandlimath T R, Umamahesh B, Sathiyanarayanan K I. J. Mol. Catal. A: Chem., 2014, 391: 198.

[15] Shang Y J, Wang C E, He X W, Ju K, Zhang M, Yu S Y, Wu J P. Tetrahedron, 2010, 66: 9629.

[16] Fan C L, He X W, Liao K S, Wang C E, Shang Y. J., Chem. Res. Chinese Universities, 2016, 32(1): 62.

[17] Wu J P, Shang Y J, Wang C E, He X W, Yan Z L, Hu M M, Zhou F Y. RSC Adv., 2013, 3: 4643.

[18] Niu Z Q, He X W, Shang Y J. Tetrahedron: Asymmetry, 2014, 25: 796.

[19] Shi G H, He X W, Shang Y J, Xiang L W, Yang C, Han G, Du B. Chin. J. Chem., 2016, 34: 901.

[20] Sheldrick G M. SHELXL-97, Program for the Refinement of Crys-tal Structures, 1997, University of Göttingen: Göttingen.