Theoretical Studies on Synthetic Mechanism of 7-Ethyl-2,2,5-trimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-8-carbonitrile

Qi-Shan Hu; Yun-Qing He; Lai-Cai Li

doi:10.14233/ajchem.2015.17391

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Issue Published : February 20, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Theoretical Studies on Synthetic Mechanism of 7-Ethyl-2,2,5-trimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-8-carbonitrile

https://doi.org/10.14233/ajchem.2015.17391

Qi-Shan Hu

College of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635711, P.R. China

Yun-Qing He

College of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635711, P.R. China

Lai-Cai Li

College of Chemistry and Material Science, Sichuan Normal University, Chengdu 610066, P.R. China

Corresponding Author(s) : Qi-Shan Hu

huqs@163.com

Asian Journal of Chemistry, Vol. 27 No. 5 (2015): Vol 27 Issue 5
Article Published : February 20, 2015

Abstract

The mechanism of one-pot synthesis among acetone, propanal and malononitrile for the synthesis of 7-ethyl-2,2,5-trimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-8-carbonitrile was investigated by density functional theory (DFT). The geometries and the frequencies of reactants, intermediates, transition states and products were calculated at the B3LYP/6-311G(d) level. The vibration analysis and the IRC analysis verified the authenticity of transition states. The reaction processes were confirmed by the changes of charge density at the bond-forming critical point. The results indicated that (1) IM3D ® IM3E is rate-determining step; (2) The activation energy of the reaction is 224.7 kJ mol^-1.

Keywords

Density functional theory Quinazolinones Malononitrile

Hu, Q.-S., He, Y.-Q., & Li, L.-C. (2015). Theoretical Studies on Synthetic Mechanism of 7-Ethyl-2,2,5-trimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-8-carbonitrile. Asian Journal of Chemistry, 27(5), 1602–1606. https://doi.org/10.14233/ajchem.2015.17391

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References

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References

T. Singh, S. Sharma, V.K. Srivastava and A. Kumar, Indian J. Chem., 45B, 2558 (2006).

V. Alagarsamy, V. Muthukumar, N. Pavalarani, P. Vasanthanathan and R. Revathi, Biol. Pharm. Bull., 26, 557 (2003); doi:10.1248/bpb.26.557.

G.P. Ouyang, P.Q. Zhang, G.F. Xu, B.A. Song, S. Yang, L.H. Jin, W. Xue, D.Y. Hu, P. Lu and Z. Chen, Molecules, 11, 383 (2006); doi:10.3390/11060383.

A.K. Nanda, S. Ganguli and R. Chakraborty, Molecules, 12, 2413 (2007); doi:10.3390/12102413.

P.M. Chandrika, T. Yakaiah, A.R.R. Rao, B. Narsaiah, N.C. Reddy, V. Sridhar and J.V. Rao, Eur. J. Med. Chem., 43, 846 (2008); doi:10.1016/j.ejmech.2007.06.010.

Z.H. Liu, X.L. Sun and S.Y. Zhang, Chin. J. Org. Chem., 21, 1161 (2001).

T.J. Luo, Z.M. Li and W.G. Zhao, Chin. J. Org. Chem., 22, 741 (2002).

H.Q. Ke, Y.X. Liu and Y.X. Zhu, J. Guangdong College Pharm., 25, 285 (2009).

X.W. Liu, H. Fu, Y.Y. Jiang and Y.F. Zhao, Angew. Chem. Int. Ed., 48, 348 (2009); doi:10.1002/anie.200804675.

J. Bergman and A. Brynolf, Tetrahedron, 46, 1295 (1990); doi:10.1016/S0040-4020(01)86694-1.

A. Witt and J. Bergman, Tetrahedron, 56, 7245 (2000); doi:10.1016/S0040-4020(00)00595-0.

D.Q. Shi and J.X. Wang, Chem. J. Chinese Univ., 25, 2051 (2004).

G.L. Dou, M.M. Wang and D.Q. Shi, J. Comb. Chem., 11, 151 (2009); doi:10.1021/cc8001469.

J.G. Zhou and J.J. Fang, Org. Chem., 76, 7730 (2011); doi:10.1021/jo201054k.

J.H. Tang, D.X. Shi, X.Z. Wang, X. Liu and J.R. Li, Chem. J. Chinese Univ., 33, 501 (2012).

R.F.W. Bader, Atoms in Molecules: A Quantum Theory; Clarendon: Oxford, UK (1990).

P.L. Prpelier, Atoms in Molecules: An Introduction; Pearson Education: Halow, UK (1999).

M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez and J.A. Pople, Gaussian, Inc.: Pittsburgh, PA (2003).

Issue

Vol. 27 No. 5 (2015): Vol 27 Issue 5

Theoretical Studies on Synthetic Mechanism of 7-Ethyl-2,2,5-trimethyl-4-oxo-1,2,3,4-tetrahydroquinazoline-8-carbonitrile

Corresponding Author(s) : Qi-Shan Hu

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