Copyright (c) 2013 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Novel Hantzsch Dihydropyridine Derivatives
Corresponding Author(s) : N. Montazeri
Asian Journal of Chemistry,
Vol. 25 No. 6 (2013): Vol 25 Issue 6
Abstract
A one-pot synthesis of novel Hantzsch dihydropyridine derivatives via a three-component cyclocondensation reaction of p-nitro acetoacetanilide, aromatic aldehyde and aqueous ammonia solution is presented. The protocol avoids the use of expensive catalyst, toxic solvent and chromatographic separation.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- R.V.A. Orru and M. de Greef, Synthesis, 1471 (2003).
- H. Bienayme, C. Hulme, G. Oddon and P. Schmitt, Chem. Eur. J., 6, 3321 (2000).
- A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000).
- L.F. Tietze and A. Modi, Med. Res. Rev., 20, 304 (2000).
- I. Ugi,A. Domling and B. Werner, J. Heterocycl. Chem., 37, 647 (2000).
- U. Einser and J. Kuthan, Chem. Rev., 72, 1 (1972).
- J. Kutan and A. Kurfurst,Ind. Eng. Chem. Prod. Res. Dev., 21, 191 (1982).
- D.M. Stout and A.I. Meyers, Chem. Rev., 82, 223 (1982).
- R. Lavilla, J. Chem. Soc., Perkin Trans. II, 1141 (2002).
- C.E. Sunkel, M.F. De Casa Juana and L. Santos, J. Med. Chem., 33, 3205 (1990).
- M. One Handkinura, Arzneim-Forsch Drug, Res., 3, 1131 (1981).
- S. Gullapalli and P. Ramarao, Neuropharmacology., 42, 467 (2002).
- B. Love, M. Goodman, K. Sander, R. Tedeschi and E. Macko, J. Med. Chem., 17, 956 (1974).
- F. Bossert, H. Meyer and E. Wehinger, Angew. Chem. Int. Engl., 20, 762 (1981).
- J.G. Breitenbucher and G. Figliozz, Tetrahedron Lett., 4, 4311 (2000).
- R. Boer and V. Gekeler, Drugs Fut., 20, 499 (1995).
- V.M. Briukhanov, Pharmacology, 57, 47 (1994).
- S. Bahekar and D. Shinde, Acta Pharm., 52, 281 (2002).
- G.A. Wachter and M.C. Davis, J. Med. Chem., 41, 2436 (1998)
- J.M. Tusell, S. Barron and J. Seratosa, J. Brain Res., 622, 99 (1993).
- N. Nakamichi, Y. Kawashita and M. Hayashi, Synthesis, 1015 (2004).
- B. Love and K.M. Sander, J. Org. Chem., 30, 1914 (1965).
- L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z. Fan, H. Tian and C.-T. Quian, Tetrahedron, 61, 1539 (2005).
- G. Sabitha, G.S.K.K. Reddy, Ch. S. Reddy and J.S. Yadav, Tetrahedron Lett., 44, 4129 (2003).
- R. Sridhar and P.T. Perumal, Tetrahedron, 61, 2465 (2005).
- B.P. Reddy, K. Rajesh and V. Vijayakumar, J. Chin. Chem. Soc., 58, 384 (2011).
- A. Donadoni, A. Massi, E. Minghini and V. Bertoasi, Tetrahedron, 60, 2311 (2004).
- B. Datta and M. Afzal Pasha, Chin. J. Catal., 32, 1180 (2011).
- M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghasemzadeh, J. Heterocycl. Chem., 42, 1021 (2005).
- N. Montazeri, Asian J. Chem., 22, 7432 (2010).
- N. Montazeri and K. Rad-Moghadam, Asian J. Chem., 18, 1557 (2006).
- 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, Phosphorus, Sulfur Silicon Rel. Elem., 179, 2533 (2004).
- B.R.P. Kumar, P. Masih, E. Karthikeyan, A. Bansal and S.P. Vijayan, Med. Chem. Res., 19, 344 (2010).
References
R.V.A. Orru and M. de Greef, Synthesis, 1471 (2003).
H. Bienayme, C. Hulme, G. Oddon and P. Schmitt, Chem. Eur. J., 6, 3321 (2000).
A. Domling and I. Ugi, Angew. Chem. Int. Ed., 39, 3168 (2000).
L.F. Tietze and A. Modi, Med. Res. Rev., 20, 304 (2000).
I. Ugi,A. Domling and B. Werner, J. Heterocycl. Chem., 37, 647 (2000).
U. Einser and J. Kuthan, Chem. Rev., 72, 1 (1972).
J. Kutan and A. Kurfurst,Ind. Eng. Chem. Prod. Res. Dev., 21, 191 (1982).
D.M. Stout and A.I. Meyers, Chem. Rev., 82, 223 (1982).
R. Lavilla, J. Chem. Soc., Perkin Trans. II, 1141 (2002).
C.E. Sunkel, M.F. De Casa Juana and L. Santos, J. Med. Chem., 33, 3205 (1990).
M. One Handkinura, Arzneim-Forsch Drug, Res., 3, 1131 (1981).
S. Gullapalli and P. Ramarao, Neuropharmacology., 42, 467 (2002).
B. Love, M. Goodman, K. Sander, R. Tedeschi and E. Macko, J. Med. Chem., 17, 956 (1974).
F. Bossert, H. Meyer and E. Wehinger, Angew. Chem. Int. Engl., 20, 762 (1981).
J.G. Breitenbucher and G. Figliozz, Tetrahedron Lett., 4, 4311 (2000).
R. Boer and V. Gekeler, Drugs Fut., 20, 499 (1995).
V.M. Briukhanov, Pharmacology, 57, 47 (1994).
S. Bahekar and D. Shinde, Acta Pharm., 52, 281 (2002).
G.A. Wachter and M.C. Davis, J. Med. Chem., 41, 2436 (1998)
J.M. Tusell, S. Barron and J. Seratosa, J. Brain Res., 622, 99 (1993).
N. Nakamichi, Y. Kawashita and M. Hayashi, Synthesis, 1015 (2004).
B. Love and K.M. Sander, J. Org. Chem., 30, 1914 (1965).
L.-M. Wang, J. Sheng, L. Zhang, J.-W. Han, Z. Fan, H. Tian and C.-T. Quian, Tetrahedron, 61, 1539 (2005).
G. Sabitha, G.S.K.K. Reddy, Ch. S. Reddy and J.S. Yadav, Tetrahedron Lett., 44, 4129 (2003).
R. Sridhar and P.T. Perumal, Tetrahedron, 61, 2465 (2005).
B.P. Reddy, K. Rajesh and V. Vijayakumar, J. Chin. Chem. Soc., 58, 384 (2011).
A. Donadoni, A. Massi, E. Minghini and V. Bertoasi, Tetrahedron, 60, 2311 (2004).
B. Datta and M. Afzal Pasha, Chin. J. Catal., 32, 1180 (2011).
M.M. Heravi, N. Montazeri, M. Rahimizadeh, M. Bakavoli and M. Ghasemzadeh, J. Heterocycl. Chem., 42, 1021 (2005).
N. Montazeri, Asian J. Chem., 22, 7432 (2010).
N. Montazeri and K. Rad-Moghadam, Asian J. Chem., 18, 1557 (2006).
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, Phosphorus, Sulfur Silicon Rel. Elem., 179, 2533 (2004).
B.R.P. Kumar, P. Masih, E. Karthikeyan, A. Bansal and S.P. Vijayan, Med. Chem. Res., 19, 344 (2010).