Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Succinimide-N-sulfonic Acid Promoted Efficient, One-Pot, Three Component Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones
Corresponding Author(s) : Sagar R. Kande
Asian Journal of Chemistry,
Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022
Abstract
A series of 2,3-dihydroquinazolin-4(1H)-ones has been synthesized using a simple, effective, one-pot, three component condensation of isatoic anhydride, aromatic aldehydes and amines in refluxing ethyl alcohol. It has been found that 15 mol% succinimide-N-sulfonic acid is the optimum amount of catalyst to obtain the high yield.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell and T.D. Greenwood, J. Med. Chem., 33, 161 (1990); https://doi.org/10.1021/jm00163a027
- J. Levin, P. Chan, T. Bailey, A. Katocs Jr. and A. Venkatesan, Bioorg. Med. Chem. Lett., 4, 1141 (1994); https://doi.org/10.1016/S0960-894X(01)80244-4
- G. Neil, L. Li, H. Buskirk and T. Moxley, Cancer Chemother., 56, 163 (1972); https://hdl.handle.net/2027/uc1.b3542203
- J. Padia, M. Field, J. Hinton, K. Meecham, J. Pablo, R. Pinnock, B. Roth, L. Singh, N. Suman-Chauhan, B. Trivedi and L. Webdale, J. Med. Chem., 41, 1042 (1998); https://doi.org/10.1021/jm970373j
- N. Abdel Gawad, H. Georgey, R. Youssef and N. El-Sayed, Eur. J. Med. Chem., 45, 6058 (2010); https://doi.org/10.1016/j.ejmech.2010.10.008
- Y. Xia, Y. Yang, M. Hour, S. Kuo, P. Xia, K. Bastow, Y. Nakanishi, P. Nampoothiri, T. Hackl, E. Hamel and K. Lee, Bioorg. Med. Chem. Lett., 11, 1193 (2001); https://doi.org/10.1016/S0960-894X(01)00190-1
- S. Sharma, K. Sharma, S. Pathak, M. Kumar and P.K. Sharma, Open Med. Chem. J., 14, 108 (2020); https://doi.org/10.2174/1874104502014010108
- S. Sharma and V. Kaur, Synthesis, 677 (1989); https://doi.org/10.1055/s-1989-27354
- J. Moore, G. Sutherland, R. Sowerby, E. Kelly, S. Palermo and W. Webster, J. Org. Chem., 34, 887 (1969); https://doi.org/10.1021/jo01256a024
- A. Shaabani, A. Maleki and H. Mofakham, Synth. Commun., 38, 3751 (2008); https://doi.org/10.1080/00397910802213802
- R. Varma, Tetrahedron, 58, 1235 (2002); https://doi.org/10.1016/S0040-4020(01)01216-9
- A. Saffar-Teluri and S. Bolouk, Monatsh. Chem., 141, 1113 (2010); https://doi.org/10.1007/s00706-010-0376-3
- Z. Karimi-Jaberi and R. Arjmandi, Monatsh. Chem., 142, 631 (2011); https://doi.org/10.1007/s00706-011-0494-6
- J. Chen, W. Su, H. Wu, M. Liu and C. Jin, Green Chem., 9, 972 (2007); https://doi.org/10.1039/b700957g
- J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding and W. Su, Tetrahedron Lett., 49, 3814 (2008); https://doi.org/10.1016/j.tetlet.2008.03.127
- A. Davoodnia, S. Allameh, A.R. Fakhari and N. Tavakoli-Hoseini, Chin. Chem. Lett., 21, 550 (2010); https://doi.org/10.1016/j.cclet.2010.01.032
- P. Salehi, M. Dabiri, M. Baghbanzadeh and M. Bahramnejad, Synth. Commun., 36, 2287 (2006); https://doi.org/10.1080/00397910600639752
- N. Khaligh, S. Hamid and S. Titinchi, Polycycl. Aromat. Compd., 37, 31 (2017); https://doi.org/10.1080/10406638.2015.1076010
- U. Chaudhar, J. Deshmukh, A. Patil and S. Kande, Int. J. Sci. Res. Sci. Eng. Technol., 9, 115 (2021); https://doi.org/10.32628/IJSRSET219523
- F. Shirini and N. Khaligh, Phosphorus Sulfur Silicon Rel. Elem., 186, 2156 (2011); https://doi.org/10.1080/10426507.2011.602377
- F. Shirini and N. Khaligh, Chin. J. Catal., 34, 695 (2013); https://doi.org/10.1016/S1872-2067(11)60499-3
- F. Shirini and N. Khaligh, Dyes Pigments, 95, 789 (2012); https://doi.org/10.1016/j.dyepig.2012.06.022
- F. Shirini and N. Khaligh, Chin. J. Catal., 34, 1890 (2013); https://doi.org/10.1016/S1872-2067(12)60669-X
- S. Kande and U. Chaudhar, Int. J. Sci. Res. Sci. Eng. Technol., 9, 105 (2021); https://doi.org/10.32628/IJSRSET219523
References
J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell and T.D. Greenwood, J. Med. Chem., 33, 161 (1990); https://doi.org/10.1021/jm00163a027
J. Levin, P. Chan, T. Bailey, A. Katocs Jr. and A. Venkatesan, Bioorg. Med. Chem. Lett., 4, 1141 (1994); https://doi.org/10.1016/S0960-894X(01)80244-4
G. Neil, L. Li, H. Buskirk and T. Moxley, Cancer Chemother., 56, 163 (1972); https://hdl.handle.net/2027/uc1.b3542203
J. Padia, M. Field, J. Hinton, K. Meecham, J. Pablo, R. Pinnock, B. Roth, L. Singh, N. Suman-Chauhan, B. Trivedi and L. Webdale, J. Med. Chem., 41, 1042 (1998); https://doi.org/10.1021/jm970373j
N. Abdel Gawad, H. Georgey, R. Youssef and N. El-Sayed, Eur. J. Med. Chem., 45, 6058 (2010); https://doi.org/10.1016/j.ejmech.2010.10.008
Y. Xia, Y. Yang, M. Hour, S. Kuo, P. Xia, K. Bastow, Y. Nakanishi, P. Nampoothiri, T. Hackl, E. Hamel and K. Lee, Bioorg. Med. Chem. Lett., 11, 1193 (2001); https://doi.org/10.1016/S0960-894X(01)00190-1
S. Sharma, K. Sharma, S. Pathak, M. Kumar and P.K. Sharma, Open Med. Chem. J., 14, 108 (2020); https://doi.org/10.2174/1874104502014010108
S. Sharma and V. Kaur, Synthesis, 677 (1989); https://doi.org/10.1055/s-1989-27354
J. Moore, G. Sutherland, R. Sowerby, E. Kelly, S. Palermo and W. Webster, J. Org. Chem., 34, 887 (1969); https://doi.org/10.1021/jo01256a024
A. Shaabani, A. Maleki and H. Mofakham, Synth. Commun., 38, 3751 (2008); https://doi.org/10.1080/00397910802213802
R. Varma, Tetrahedron, 58, 1235 (2002); https://doi.org/10.1016/S0040-4020(01)01216-9
A. Saffar-Teluri and S. Bolouk, Monatsh. Chem., 141, 1113 (2010); https://doi.org/10.1007/s00706-010-0376-3
Z. Karimi-Jaberi and R. Arjmandi, Monatsh. Chem., 142, 631 (2011); https://doi.org/10.1007/s00706-011-0494-6
J. Chen, W. Su, H. Wu, M. Liu and C. Jin, Green Chem., 9, 972 (2007); https://doi.org/10.1039/b700957g
J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding and W. Su, Tetrahedron Lett., 49, 3814 (2008); https://doi.org/10.1016/j.tetlet.2008.03.127
A. Davoodnia, S. Allameh, A.R. Fakhari and N. Tavakoli-Hoseini, Chin. Chem. Lett., 21, 550 (2010); https://doi.org/10.1016/j.cclet.2010.01.032
P. Salehi, M. Dabiri, M. Baghbanzadeh and M. Bahramnejad, Synth. Commun., 36, 2287 (2006); https://doi.org/10.1080/00397910600639752
N. Khaligh, S. Hamid and S. Titinchi, Polycycl. Aromat. Compd., 37, 31 (2017); https://doi.org/10.1080/10406638.2015.1076010
U. Chaudhar, J. Deshmukh, A. Patil and S. Kande, Int. J. Sci. Res. Sci. Eng. Technol., 9, 115 (2021); https://doi.org/10.32628/IJSRSET219523
F. Shirini and N. Khaligh, Phosphorus Sulfur Silicon Rel. Elem., 186, 2156 (2011); https://doi.org/10.1080/10426507.2011.602377
F. Shirini and N. Khaligh, Chin. J. Catal., 34, 695 (2013); https://doi.org/10.1016/S1872-2067(11)60499-3
F. Shirini and N. Khaligh, Dyes Pigments, 95, 789 (2012); https://doi.org/10.1016/j.dyepig.2012.06.022
F. Shirini and N. Khaligh, Chin. J. Catal., 34, 1890 (2013); https://doi.org/10.1016/S1872-2067(12)60669-X
S. Kande and U. Chaudhar, Int. J. Sci. Res. Sci. Eng. Technol., 9, 105 (2021); https://doi.org/10.32628/IJSRSET219523