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Synthesis of Spiro Heterobicyclic Rings Using Cellulose Sulfuric Acid Under Solvent Free Conditions
Corresponding Author(s) : Naser Montazeri
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
Cellulose sulfuric acid is found to be a heterogenic recyclable catalyst for the rapid and efficient synthesis spiro heterobicyclic rings via a three component condensation reaction between aldehydes, barbituric acid and urea (or thiourea) under solvent-free conditions. The method offers several advantages, including high yields, short reaction times, simple work-up procedure and reusability of the catalyst. We believe that this applicability of cellulose sulfuric acid with mention advantages makes our method superior over all reported methods to the synthesis of spiro heterobicyclic compounds.
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- R.V.A. Orru and M. deGreef, Synthesis, 1471 (2003).
- L.F. Tietze and A. Modi, Med. Res. Rev., 20, 304 (2000).
- I. Ugi,A. Domling and B. Werner, J. Heterocyc. Chem., 37, 647 (2000).
- J.L. Mokrosz, M.H. Psluchowska, E. Szneler and B. Drozdz, Arch. Chem., 322, 231 (1989).
- A.C. Cope, P. Kovacic and M. Burg, J. Am. Chem. Soc., 71, 3656 (1949)
- M.I. Al-Ashmawi, K.M. Ghoneim and M. Khalifa, Pharmaze, 35, 591 (1980).
- W.O. Foye, Principle of Medicinal Chemistry (Lea and Febiger, London) 159 (1989).
- L.S. Goodman and A. Gilman, The Pharmacological Basis of Therapeutics (McGraw-Hill, New Delhi) p. 358 (1991).
- H. Arimoto, I. Hayakawa, M. Kuramoto and D. Uemure, Tetrahedron Lett., 36, 861 (1998).
- T. Chou, M. Kuramoto, Y. Otani, M. Shkano, K. Yazawa and D. Uemere, Tetrahedron Lett., 37, 387 (1996).
- T. Tokuyama, K. Uenoyama, G. Brown, J.W. Daly and B. Witkop, Helv. Chim. Acta, 57, 2597 (1974).
- M. Kuramoto, C. Tong, K. Yamada, T. Chiba, Y. Hayacshi and D. Uemura, Tetrahedron Lett., 37, 3867 (1996).
- K.F. Shelke, S.B. Spakal, G.K. Kakade, B.B. Shingate and M.S. Shingare, Green Chem. Lett. Rev., 3, 27 (2010).
- D. Parajapati, D. Bhaugan, M. Gohain and W. Hu, Mol. Divers, 15, 257 (2011).
- A. Shaabani and A. Bazgir, Tetrahed. Lett., 45, 2575 (2004).
- D. Klemm, B. Heublein, H.P. Fink and A. Bohn, Angew. Chem. Int. Ed., 44, 3358 (2005).
- P.N. Reddy, Y.T. Reddy, M.N. Reddy, B. Rajitha and P.A. Crooks, Synth. Commun., 39, 1257 (2009).
- A. Shaabani, A. Ranmati and Z. Badri, Catal. Comm., 9, 13 (2008).
- S.A. Sadaphal, S.S. Sonar, M.N. Ware and M.S. Shingare, Green Chem. Lett. Rev., 1, 191 (2008).
- A. Shaabani, A.H. Rezayan, M. Behnam and M. Heidary, C.R. Chimie, 12, 1249 (2009).
- B.S. Kuarm, J.V. Madhav, B. Rajitha, Y.T. Reddy, P.N. Reddy and P.A. Crooks, Syn. Commun., 41, 662 (2011).
- J.V. Madhav, Y.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks and B. Rajitha, J. Mol. Catal. A, 304, 85 (2009).
- N. Montazeri and K, Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008).
- N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011).
- N. Montazeri and K. Rad-Moghadam, Phosphona, Sulfur, Silicon Rel. Elem., 179, 2533 (2004).
- N. Montazeri, Asian J. Chem., 22, 7432 (2010).
- N. Montazeri and K. Rad-Moghadam, Asian J. Chem., 18, 1557 (2006).
- F. Hatamjafari, N. Montazeri and K. Pourshamsian, Asian J. Chem., 23, 3287 (2011).
References
R.V.A. Orru and M. deGreef, Synthesis, 1471 (2003).
L.F. Tietze and A. Modi, Med. Res. Rev., 20, 304 (2000).
I. Ugi,A. Domling and B. Werner, J. Heterocyc. Chem., 37, 647 (2000).
J.L. Mokrosz, M.H. Psluchowska, E. Szneler and B. Drozdz, Arch. Chem., 322, 231 (1989).
A.C. Cope, P. Kovacic and M. Burg, J. Am. Chem. Soc., 71, 3656 (1949)
M.I. Al-Ashmawi, K.M. Ghoneim and M. Khalifa, Pharmaze, 35, 591 (1980).
W.O. Foye, Principle of Medicinal Chemistry (Lea and Febiger, London) 159 (1989).
L.S. Goodman and A. Gilman, The Pharmacological Basis of Therapeutics (McGraw-Hill, New Delhi) p. 358 (1991).
H. Arimoto, I. Hayakawa, M. Kuramoto and D. Uemure, Tetrahedron Lett., 36, 861 (1998).
T. Chou, M. Kuramoto, Y. Otani, M. Shkano, K. Yazawa and D. Uemere, Tetrahedron Lett., 37, 387 (1996).
T. Tokuyama, K. Uenoyama, G. Brown, J.W. Daly and B. Witkop, Helv. Chim. Acta, 57, 2597 (1974).
M. Kuramoto, C. Tong, K. Yamada, T. Chiba, Y. Hayacshi and D. Uemura, Tetrahedron Lett., 37, 3867 (1996).
K.F. Shelke, S.B. Spakal, G.K. Kakade, B.B. Shingate and M.S. Shingare, Green Chem. Lett. Rev., 3, 27 (2010).
D. Parajapati, D. Bhaugan, M. Gohain and W. Hu, Mol. Divers, 15, 257 (2011).
A. Shaabani and A. Bazgir, Tetrahed. Lett., 45, 2575 (2004).
D. Klemm, B. Heublein, H.P. Fink and A. Bohn, Angew. Chem. Int. Ed., 44, 3358 (2005).
P.N. Reddy, Y.T. Reddy, M.N. Reddy, B. Rajitha and P.A. Crooks, Synth. Commun., 39, 1257 (2009).
A. Shaabani, A. Ranmati and Z. Badri, Catal. Comm., 9, 13 (2008).
S.A. Sadaphal, S.S. Sonar, M.N. Ware and M.S. Shingare, Green Chem. Lett. Rev., 1, 191 (2008).
A. Shaabani, A.H. Rezayan, M. Behnam and M. Heidary, C.R. Chimie, 12, 1249 (2009).
B.S. Kuarm, J.V. Madhav, B. Rajitha, Y.T. Reddy, P.N. Reddy and P.A. Crooks, Syn. Commun., 41, 662 (2011).
J.V. Madhav, Y.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks and B. Rajitha, J. Mol. Catal. A, 304, 85 (2009).
N. Montazeri and K, Rad-Moghadam, Chin. Chem. Lett., 19, 1143 (2008).
N. Montazeri, S. Khaksar, A. Nazari, S.S. Alavi, S.M. Vahdat and M. Tajbakhsh, J. Fluorine Chem., 132, 450 (2011).
N. Montazeri and K. Rad-Moghadam, Phosphona, Sulfur, Silicon Rel. Elem., 179, 2533 (2004).
N. Montazeri, Asian J. Chem., 22, 7432 (2010).
N. Montazeri and K. Rad-Moghadam, Asian J. Chem., 18, 1557 (2006).
F. Hatamjafari, N. Montazeri and K. Pourshamsian, Asian J. Chem., 23, 3287 (2011).