One-Pot Three Component Cascade Synthesis of Fused Ring Quinazoline-2,4-dione Derivatives Employing Heterocyclic Ketene Aminals as a Versatile Synthone

Muhammad Yaqub; Nadia Arif; Ruqayia Perveen; Javaria Batool; Muhammad Tariq Riaz; Muhammad Yaseen

doi:10.14233/ajchem.2015.18004

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

Issue Published : January 19, 2015

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

One-Pot Three Component Cascade Synthesis of Fused Ring Quinazoline-2,4-dione Derivatives Employing Heterocyclic Ketene Aminals as a Versatile Synthone

https://doi.org/10.14233/ajchem.2015.18004

Muhammad Yaqub

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Nadia Arif

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Ruqayia Perveen

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Javaria Batool

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Muhammad Tariq Riaz

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan

Muhammad Yaseen

Mohi-u-Din Institute Pharmaceutical Sciences, Mohi-u-Din Islamic University, Mirpur, Pakistan

Corresponding Author(s) : Muhammad Yaqub

mayaqub2@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 3 (2015): Vol 27 Issue 3
Article Published : January 18, 2015

Abstract

One-pot three component cascade protocol for the synthesis of quinazoline-2,4-dione derivatives was designed and a series of twenty fused ring quinazoline-2,4-dione derivatives 11a-11j and 12a-12j were synthesized by the reaction of heterocyclic ketene aminal, barbituric acid and benzaldehyde. Structure of all the synthesized quinazoline-2,4-dione derivatives was established on the basis of analytical (C, H, N) and spectroscopic (¹H NMR, ¹³C NMR and mass) data and mechanism for the cascade reaction was proposed.

Keywords

Heterocyclic ketene aminal Barbituric acid Quinazoline-2 4-dione Cascade synthesis

Yaqub, M., Arif, N., Perveen, R., Batool, J., Tariq Riaz, M., & Yaseen, M. (2015). One-Pot Three Component Cascade Synthesis of Fused Ring Quinazoline-2,4-dione Derivatives Employing Heterocyclic Ketene Aminals as a Versatile Synthone. Asian Journal of Chemistry, 27(3), 1013–1018. https://doi.org/10.14233/ajchem.2015.18004

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References

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M. Yaqub, R. Perveen, Z. Shafiq, H. Pervez and M.N. Tahir, Synlett, 1755 (2012); doi:10.1055/s-0031-1289787.
S.-J. Yan, C. Huang, X.-H. Zeng, R. Huang and J. Lin, Bioorg. Med. Chem. Lett., 20, 48 (2010); doi:10.1016/j.bmcl.2009.11.044.
M.-X. Zhao, M.-X. Wang and Z.-T. Huang, Tetrahedron, 58, 1309 (2002); doi:10.1016/S0040-4020(02)00002-9.
M. Yaqub, C.-Y. Yu, Y.-M. Jia and Z.-T. Haung, Synlett, 1357 (2008); doi:10.1055/s-2008-1072788.
W.-Y. Xu, Y.-M. Jia, J.-K. Yang, Z.-T. Huang and C.-Y. Yu, Synlett, 1682 (2010); doi:10.1055/s-0029-1220126.
J.-P. Laio, T. Zhang, C.-Y. Yu and Z.-T. Haung, Synlett, 761 (2007); doi:10.1055/s-2007-970757.
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References

J. Penn, P.G. Mantle, J.N. Bilton and R.N. Sheppard, J. Chem. Soc., Perkin Trans I, 1495 (1992); doi:10.1039/p19920001495.

M.M. Abdelhalim, M.M.T.S.T. El-Saidi, S.T. Rabie and G.A. Elmegeed, Steroids, 72, 459 (2007); doi:10.1016/j.steroids.2007.01.003.

H. Kondo, M. Taguchi, Y. Inoue, F. Sakamoto and G. Tsukamoto, J. Med. Chem., 33, 2012 (1990); doi:10.1021/jm00169a033.

T.-C. Chou, K.M. Depew, Y.-H. Zheng, M.L. Safer, M.G. Chan, B. Helfrich, D. Zatorska, A. Zatorski, W. Bornmann and S.J. Danishefsky, Proc. Natl. Acad. Sci. USA, 95, 8369 (1998); doi:10.1073/pnas.95.14.8369.

S.N. Suryawanshi, S. Pandey, Rashmirathi, B.A. Bhatt and S. Gupta, Eur. J. Med. Chem., 42, 511 (2007); doi:10.1016/j.ejmech.2006.09.016.

F. Hernández, F.L. Buenadicha, C. Avendaño and M. Söllhuber, Tetrahedron Asymm., 12, 3387 (2002); doi:10.1016/S0957-4166(02)00027-7.

F. Yu, S. Yan, L. Hu, Y. Wang and J. Lin, Org. Lett., 13, 4782 (2011); doi:10.1021/ol201783d.

S. Yan, C. Huang, C. Su, Y. Ni and J. Lin, J. Comb. Chem., 12, 91 (2010); doi:10.1021/cc900121c.

M. Li, P. Shao, S.-W. Wang, W. Kong and L.-R. Wen, J. Org. Chem., 77, 8956 (2012); doi:10.1021/jo3013836.

M.-X. Zhao, Z.-M. Wang, M.-X. Wang, C.H. Yan and Z.-T. Huang, Tetrahedron, 58, 7791 (2002); doi:10.1016/S0040-4020(02)00945-6.

A. Rezvanian and A. Alizadeh, Tetrahedron, 68, 10164 (2012); doi:10.1016/j.tet.2012.09.101.

X.-M. Chen, Z.-J. Li and Z.-T. Huang, Carbohydr. Res., 328, 253 (2000); doi:10.1016/S0008-6215(00)00122-1.

M.-X. Wang, W.-S. Miao, Y. Cheng and Z.-T. Huang, Tetrahedron, 55, 14611 (1999); doi:10.1016/S0040-4020(99)00937-0.

X.-P. Nie, M.-X. Wang and Z.-T. Huang, Synthesis, 1439 (2000); doi:10.1055/s-2000-7098.

M.-X. Zhao, Z.-M. Wang, M.-X. Wang, C.-H. Yan and Z.-T. Huang, Tetrahedron, 58, 7791 (2002); doi:10.1016/S0040-4020(02)00945-6.

M. Yaqub, R. Perveen, Z. Shafiq, H. Pervez and M.N. Tahir, Synlett, 1755 (2012); doi:10.1055/s-0031-1289787.

S.-J. Yan, C. Huang, X.-H. Zeng, R. Huang and J. Lin, Bioorg. Med. Chem. Lett., 20, 48 (2010); doi:10.1016/j.bmcl.2009.11.044.

M.-X. Zhao, M.-X. Wang and Z.-T. Huang, Tetrahedron, 58, 1309 (2002); doi:10.1016/S0040-4020(02)00002-9.

M. Yaqub, C.-Y. Yu, Y.-M. Jia and Z.-T. Haung, Synlett, 1357 (2008); doi:10.1055/s-2008-1072788.

W.-Y. Xu, Y.-M. Jia, J.-K. Yang, Z.-T. Huang and C.-Y. Yu, Synlett, 1682 (2010); doi:10.1055/s-0029-1220126.

J.-P. Laio, T. Zhang, C.-Y. Yu and Z.-T. Haung, Synlett, 761 (2007); doi:10.1055/s-2007-970757.

C.-Y. Yu, P.-H. Yang, M.-X. Zhao and Z.-T. Huang, Synlett, 1835 (2006); doi:10.1055/s-2006-947343.

Z.-T. Huang and Z.-R. Liu, Synth. Commun., 19, 943 (1989); doi:10.1080/00397918908051014.

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

One-Pot Three Component Cascade Synthesis of Fused Ring Quinazoline-2,4-dione Derivatives Employing Heterocyclic Ketene Aminals as a Versatile Synthone

Corresponding Author(s) : Muhammad Yaqub

Abstract

Keywords

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