Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones

Abdullah S. Al-Bogami; Hamad Z. Alkhathlan; Tamer S. Saleh

doi:10.14233/ajchem.2013.15070

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Issue Published : May 18, 2013

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

Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones

https://doi.org/10.14233/ajchem.2013.15070

Abdullah S. Al-Bogami

Department of Chemistry, Faculty of Science, King Abdulaziz University, North Jeddah, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Hamad Z. Alkhathlan

Department of Chemistry, Faculty of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia

Tamer S. Saleh

Department of Chemistry, Faculty of Science, King Abdulaziz University, North Jeddah, P.O. Box 80203, Jeddah 21589, Saudi Arabia

Corresponding Author(s) : Abdullah S. Al-Bogami

chem_org@hotmail.com

Asian Journal of Chemistry, Vol. 25 No. 11 (2013): Vol 25 Issue 11
Article Published : June 6, 2013

Abstract

Hydroxy chalcones undergo simple cyclizations with phenylhydrazine to afford 2-pyrazolines under microwave irradiation in the presence of glacial AcOH as cyclizing agent, also undergo simple cyclizations with hydroxylamine to afford 2-isoxazolines under microwave irradiation in the presence of KOH, and new cyclohexenone derivatives. Some valuable intermediates in the synthesis of fused heterocycles, have been prepared through K₂CO₃ which activate the cyclocondensation of hydroxychalcones with ethyl acetoacetate. The obtained results indicate that the microwave irradiation give shorter reaction times and cleaner reactions for synthesis of biologically important compounds.

Keywords

2-Pyrazolines 2-Isoxazolines Cyclohexenone Hydroxy Chalcone Microwave Irradiation

S. Al-Bogami, A., Z. Alkhathlan, H., & S. Saleh, T. (2013). Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones. Asian Journal of Chemistry, 25(11), 6427–6433. https://doi.org/10.14233/ajchem.2013.15070

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References

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References

M.A. El.Hashah, M. El-Kady, M.A. Saiyed and A.A. Elaswy, Egypt. J. Chem., 27, 715 (1985).

L.S. Crawley and W.J. Fanshawe, J. Heterocycl. Chem., 14, 531 (1977).

E.C. Taylor and R.W. Morrison, J. Org. Chem., 32, 2379 (1967).

P.S. Utale, P.B. Raghuvanshi and A.G. Doshi, Asian J. Chem., 10, 597 (1998).

K. Ramalingham, G.X. Thyvekikakath, K.D. Berlin, R.W. Chesnut, R.A. Brown, N.N. Durham,A.E. Ealick and D. van der Helm, J. Med. Chem., 20, 847 (1977).

R.E. Brown and J. Shavrel, US Patent, 624,102 (1972); Chem. Abstr., 76, 59618 (1972).

J.G. Lombardino and I.G. Otterness, J. Med. Chem., 24, 830 (1981).

L.C. Raiford and W.J. Peterson, J. Org. Chem., 1, 544 (1936).

L.C. Raiford and G.V. Gundy, J. Org. Chem., 3, 265 (1938).

L.C. Raiford and R.H. Manley, J. Org. Chem., 5, 590 (1940).

W. Ried and G. Dankert, Chem. Ber., 90, 2707 (1957).

R.H. Wiley, C.H. Jarboe, F.N. Hayes, E. Hansbury, J.T. Nielsen, P.X. Callahan and M.C. Sellars, J. Org. Chem., 23, 732 (1958).

A.E.A. Sammour, Tetrahedron, 20, 1067 (1964).

I. Bhatnagar and M.V. George, Tetrahedron, 24, 1293 (1968).

J.L. Aubagnac, J. Elguero and R. Jacquier, Bull. Soc. Chim. Fr., 3292 (1969).

F.G. Weber, K. Brosche, C. Seedorf and A. Rinow, Monatsh. Chem., 100, 1924 (1969).

M.G. Joshi and K.N. Wadodkar, Indian J. Chem., 20B, 1090 (1981).

T.C. Sharma, S.R. Pawar and N.J. Reddy, Acta Chim. Hung, 112, 159 (1983).

D.N. Dhar and R. Raghunathan, Indian J. Chem., 23B, 1187 (1984).

V.D. Orlov, M.A. Aziz, N.O. Mchedlov-Petrosyan and P.K.D. Asoka, Khim. Geterotsikl. Soedin., 1511 (1985).

V. Padmavathi, K. Sharmila,A. Somasekhar and D. Bhaskar, Indian J. Chem, 40B, 11 (2001).

D.B. Reddy, A.S. Reddy and V. Padmavathi, J. Chem. Res. (S), 784 (1998).

S. Samshuddin, B. Narayan, B.K. Sarojini, H.S. Yathirajan and R. Raghavendra, Der Pharma Chemica, 4, 1445 (2012).

C. Chen, K.M. Wilcoxen, C.Q. Huang, J.R. McCarthy, T. Chen and D.E. Grigoriadis, Bioorg. Med. Chem. Lett., 14, 3669 (2004).

A.S. Albogami, Asian J .Chem., 23, 3045 (2011).

A.S. Albogami, A.M. Almajid, M.A. Al-Saad, A.M. Mosa, S.A. Almazroa and H.Z. Alkhathlan, Molecules, 14, 2147 (2009).

A.S. Albogami, Synthetic Commun., 41, 2952 (2011).

A.S. Albogami, U. Karama, A.A. Mousa, V. Khan, S.A. Al-mazroa and H.Z. Alkhathlan, Oriental J. Chem., 28, 619 (2012).

A. Lévai and J. Jekob, Arkivoc, 10, 199 (2005).

L. Jurd, Tetrahedron, 31, 2884 (1975).

W. Davey and J.R. Gwilt, J. Chem. Soc., 1015 (1957).

J.A. VanAllan and G.A. Reynolds, J. Org. Chem., 33, 1102 (1968).

A. Sammour, M.T. Elzimaity and A. Abdel-Maksoud, J. Chem. U.A.R., 12, 481 (1969).

Issue

Vol. 25 No. 11 (2013): Vol 25 Issue 11

Microwave Enhanced Green Synthesis of 2-Pyrazolines, Isoxazolines and Cyclohexenones

Corresponding Author(s) : Abdullah S. Al-Bogami

Abstract

Keywords

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