DBU As A Novel and Highly Efficient Catalyst for The Synthesis of 3,5-Disubstituted-2,6-dicyanoanilines Under Conventional and Microwave Conditions

Document Type: Research Note

Authors

1 School of Studies in Chemistry, Vikram University, Ujjain, Madhya Pradesh, 456010, INDIA

2 Department of Physics, Lovely Professional University, Phagwara, Punjab, 144411, INDIA

Abstract

3,5-disubstituted-2,6-dicyanoaniline derivatives have been synthesized via the reaction of aryl methylene- and 1-arylethylidenemalonodinitriles using 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) as a  novel and highly efficient catalyst under conventional as well as microwave conditions. Use of non-hazardous, inexpensive and readily available base catalyst, convenient procedure, short reaction time and improved product yields are some added advantages of the present protocol.

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[1] Borate H.B., Kudale A.S., Agalave S.G., Synthesis of Substituted 2,6-Dicyanoanilines and Related Compounds. A Review, Organic Preparations and Procedures International, 44: 467-521 (2012).

[3] Griffiths J., Lockwood M., Roozpeikar B., Orientation Effects in The Benzene Chromophore Bearing One Donor and Two Acceptor Groups. Electronic Absorption Spectra of The Dicyanoanilines, J. Chem. Soc. Perkin Trans. 2, 1608-1610 (1977).

[4] Prasad P.N., Williams D.J., "Introduction to Nonlinear Optical Effects in Molecules and Polymers", John Wiley, New York, (1991).

[5] Kurreck H., Huber M., Model Reactions for Photosynthesis-Photoinduced Charge and Energy Transfer Between Covalently Linked Porphyrin and Quinone Units, Angew. Chem. Int. Ed., 34: 849-866 (1995). [6] Petty M.C., Bryce M.R., Bloor D., "Introduction to Molecular Electronics”, Oxford University Press: New York, (1995).

[7] Raghukumar V., Murugan P., Ramakrishnan V.T., A Facile One Pot Synthesis of m-Terphenyl and Biaryl Derivatives, Synth. Commun., 31: 3497-3505 (2001).

[9] Milart P., Wilamowski J., Sepiol J.J., Synthesis of Di-  andTriamino-l,l':3',l"-terphenyls from Arylethylidene- and Arylidenemalonodinitriles,Tetrahedron., 54: 15643-15656  (1998).

[11] Shaterian H.R., Honarmand M., Oveisi A.R., Multicomponent Synthesis of 3,5-Diaryl-2,6-Dicyanoanilines Under Thermal Solvent-Free Conditions, Monatsh. Chem., 141: 557-560 (2010).

[13] Ashry E.S.H.El., Kassem A.A., Account of Microwave Irradiation for Accelerating Organic Reactions, ARKIVOC., ix: 1-16 (2006).

[14] Elander N., Jones J.R., Lu S.Y., Elander S.S.,   Microwave-Enhanced Radiochemistry, Chem. Soc. Rev., 29: 239-249 (2000).

[15] Aggarwal V.K., Mereu A., Superior Amine Catalysts for The Baylis-Hillman Reaction : The Use of DBU and Its Implication, Chem. Commun., 2311-2312 (1999).

[16] Yeom C.E., Kim M.J., Kim M.B., 1,8-Diazabicyclo[5.4.0]Undec-7-Ene (DBU) Promoted Efficient and Versatile Aza-Michael Addition, Tetrahedron, 63: 904-909 (2007).

[21] Xin X., Wang Y., Xu W., Lin Y., Duan H., Dong D., A Facile and Efficient One-Pot Synthesis of Polysubstituted Benzenes in Guanidinium Ionic Liquids, Green Chem. 12: 893-898 (2010).