One Pot, Four Component Synthesis of Phthalazine-1,4-diones Derivatives in [BMIM][OH] Medium

D.P. Loka Maheshwari; B. Satyanarayana

doi:10.14233/ajchem.2020.22180

Issue

Vol. 32 No. 1 (2020): Vol 32 Issue 1

Issue Published : September 18, 2019

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

One Pot, Four Component Synthesis of Phthalazine-1,4-diones Derivatives in [BMIM][OH] Medium

https://doi.org/10.14233/ajchem.2020.22180

D.P. Loka Maheshwari

GVK Biosciences Private Limited, IDA Nacharam, Hyderabad-500076, India

B. Satyanarayana

Macleods Pharmaceutical ltd, Kondivita Rd, Marol MIDC Industry Estate Andheri East, Mumbai-400093, India

Corresponding Author(s) : D.P. Loka Maheshwari

lokamaheshwari123@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 1 (2020): Vol 32 Issue 1
Article Published : November 18, 2019

Abstract

[BMIM][OH] mediated, green and efficient synthesis of phthalazines (5) have been developed by condensing diethyl phthalate (1), ethyl cyanohydrazide (2), substituted benzaldehyde (3) and malononitrile (4) in the presence of Meldrum’s acid at 60-65 °C and at room temperature for 60-90 min. The importance of this method includes shorter reaction time and high yield.

Keywords

Diethyl phthalate benzaldehydes Ethyl cyanohydrazide Meldrum’s acid Ionic liquids

Loka Maheshwari, D., & Satyanarayana, B. (2019). One Pot, Four Component Synthesis of Phthalazine-1,4-diones Derivatives in [BMIM][OH] Medium. Asian Journal of Chemistry, 32(1), 45–48. https://doi.org/10.14233/ajchem.2020.22180

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References

A.M. Inamuddin, Green Solvents I, Properties and Applications of Ionic Liquids, Springer: United Kingdom (2012).
A.M. Inamuddin, Green Solvents II: Properties and Applications of Ionic Liquids, Springer, United Kingdom (2012).
P. Tundo, A. Perosa and F. Zecchini, Methods and Reagents for Green Chemistry: An Introduction, Wiley, New Jersey (2007).
P. Wasserscheid and P. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Germany (2003).
C. Montagne, J.J. Shiers and M. Shipman, Tetrahedron Lett., 47, 9207 (2006); https://doi.org/10.1016/j.tetlet.2006.10.135.
M. Haji, Beilstein J. Org. Chem., 12, 1269 (2016); https://doi.org/10.3762/bjoc.12.121.
A. Varadi, T.C. Palmer, R.D. Notis and S. Majumdar, Molecules, 21, 19 (2015); https://doi.org/10.3390/molecules21010019.
F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem. J., 36, 598 (2002); https://doi.org/10.1023/A:1022665331722.
A.M. Jadhav, S.G. Balwe, J.S. Kim, K.T. Lim and Y.T. Jeong, Tetrahedron Lett., 60, 560 (2019); https://doi.org/10.1016/j.tetlet.2019.01.028.
R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Leeson, S. Thomas, D. O’Connor, R.M. McKernan, K. Quirk, S.M. Cook, J.R. Atack, K.A. Wafford, S.A. Thompson, G.R. Dawson, P. Ferris and J.L. Castro, J. Med. Chem., 47, 1807 (2004); https://doi.org/10.1021/jm031020p
R.P. Jain and J.C. Vederas, Bioorg. Med. Chem. Lett., 14, 3655 (2004); https://doi.org/10.1016/j.bmcl.2004.05.021.
S.G. Balwe and Y.T. Jeong, Org. Biomol. Chem., 16, 1287 (2018); https://doi.org/10.1039/c7ob02933k.
S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi and C. De Micheli, J. Med. Chem., 43, 2851 (2000); https://doi.org/10.1021/jm001002x.
Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura and K. Kubo, Chem. Pharm. Bull. (Tokyo), 38, 2179 (1990); https://doi.org/10.1248/cpb.38.2179.
N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama and H. Adachi, J. Med. Chem., 41, 3367 (1998); https://doi.org/10.1021/jm970815r.
T. Sheradsky and R. Moshenberg, J. Org. Chem., 51, 3123 (1986); https://doi.org/10.1021/jo00366a008.
H.W. Heine, L.M. Baclawski, S.M. Bonser and G.D. Wachob, J. Org. Chem., 41, 3229 (1976); https://doi.org/10.1021/jo00882a002.
Y.K. Ramtohul, M.N.G. James and J.C. Vederas, J. Org. Chem., 67, 3169 (2002); https://doi.org/10.1021/jo0157831.
L.P. Liu, J.M. Lu and M. Shi, Org. Lett., 9, 1303 (2007); https://doi.org/10.1021/ol070178r.
J. Volmajer, R. Toplak, S. Bittner and A.M.L. Marechala, ARKIVOC, 49 (2003); https://doi.org/10.3998/ark.5550190.0004.e06.
P.P. Kumar, Y.D. Reddy, Ch.V.R. Reddy, B.R. Devi and P.K. Dubey, Tetrahedron Lett., 55, 2177 (2014); https://doi.org/10.1016/j.tetlet.2014.02.020.

References

A.M. Inamuddin, Green Solvents I, Properties and Applications of Ionic Liquids, Springer: United Kingdom (2012).

A.M. Inamuddin, Green Solvents II: Properties and Applications of Ionic Liquids, Springer, United Kingdom (2012).

P. Tundo, A. Perosa and F. Zecchini, Methods and Reagents for Green Chemistry: An Introduction, Wiley, New Jersey (2007).

P. Wasserscheid and P. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Germany (2003).

C. Montagne, J.J. Shiers and M. Shipman, Tetrahedron Lett., 47, 9207 (2006); https://doi.org/10.1016/j.tetlet.2006.10.135.

M. Haji, Beilstein J. Org. Chem., 12, 1269 (2016); https://doi.org/10.3762/bjoc.12.121.

A. Varadi, T.C. Palmer, R.D. Notis and S. Majumdar, Molecules, 21, 19 (2015); https://doi.org/10.3390/molecules21010019.

F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem. J., 36, 598 (2002); https://doi.org/10.1023/A:1022665331722.

A.M. Jadhav, S.G. Balwe, J.S. Kim, K.T. Lim and Y.T. Jeong, Tetrahedron Lett., 60, 560 (2019); https://doi.org/10.1016/j.tetlet.2019.01.028.

R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Leeson, S. Thomas, D. O’Connor, R.M. McKernan, K. Quirk, S.M. Cook, J.R. Atack, K.A. Wafford, S.A. Thompson, G.R. Dawson, P. Ferris and J.L. Castro, J. Med. Chem., 47, 1807 (2004); https://doi.org/10.1021/jm031020p

R.P. Jain and J.C. Vederas, Bioorg. Med. Chem. Lett., 14, 3655 (2004); https://doi.org/10.1016/j.bmcl.2004.05.021.

S.G. Balwe and Y.T. Jeong, Org. Biomol. Chem., 16, 1287 (2018); https://doi.org/10.1039/c7ob02933k.

S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi and C. De Micheli, J. Med. Chem., 43, 2851 (2000); https://doi.org/10.1021/jm001002x.

Y. Nomoto, H. Obase, H. Takai, M. Teranishi, J. Nakamura and K. Kubo, Chem. Pharm. Bull. (Tokyo), 38, 2179 (1990); https://doi.org/10.1248/cpb.38.2179.

N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama and H. Adachi, J. Med. Chem., 41, 3367 (1998); https://doi.org/10.1021/jm970815r.

T. Sheradsky and R. Moshenberg, J. Org. Chem., 51, 3123 (1986); https://doi.org/10.1021/jo00366a008.

H.W. Heine, L.M. Baclawski, S.M. Bonser and G.D. Wachob, J. Org. Chem., 41, 3229 (1976); https://doi.org/10.1021/jo00882a002.

Y.K. Ramtohul, M.N.G. James and J.C. Vederas, J. Org. Chem., 67, 3169 (2002); https://doi.org/10.1021/jo0157831.

L.P. Liu, J.M. Lu and M. Shi, Org. Lett., 9, 1303 (2007); https://doi.org/10.1021/ol070178r.

J. Volmajer, R. Toplak, S. Bittner and A.M.L. Marechala, ARKIVOC, 49 (2003); https://doi.org/10.3998/ark.5550190.0004.e06.

P.P. Kumar, Y.D. Reddy, Ch.V.R. Reddy, B.R. Devi and P.K. Dubey, Tetrahedron Lett., 55, 2177 (2014); https://doi.org/10.1016/j.tetlet.2014.02.020.

Issue

Vol. 32 No. 1 (2020): Vol 32 Issue 1

One Pot, Four Component Synthesis of Phthalazine-1,4-diones Derivatives in [BMIM][OH] Medium

Corresponding Author(s) : D.P. Loka Maheshwari

Abstract

Keywords

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