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An Expedient Synthesis of 2-Aryl-substituted 2,3-Dihydroquinazolin-4(1H)-ones in Low Transition Temperature Mixture (LTTM) containing SnCl2 and L-Proline
Asian Journal of Chemistry,
Vol. 34 No. 7 (2022): Vol 34 Issue 7, 2022
Abstract
2,3-Dihydroquinazolin-4(1H)-ones were synthesized in excellent yield in a prepared low transition temperature mixture (LTTM) containing SnCl2 and L-proline using either direct one-pot two-component cyclocondensation of anthranilamide and aldehydes or one-pot three-component cyclocondensation of isatoic anhydride, ammonium acetate and aldehydes. The prepared LTTM is a green solvent, inexpensive, non-toxic and serves a dual function as reusable catalyst and solvent with excellent reaction endorsing medium. The current protocol has several advantages including an easy work up, shorter reaction time, high yield with a higher atom economy and maximum reaction efficiency with excellent green chemistry metrics.
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- M.R. Yadav, S.T. Shirude, A. Parmar, R. Balaraman and R. Giridhar, Chem. Heterocycl. Compd., 42, 1038 (2006); https://doi.org/10.1007/s10593-006-0201-4
- R.J. Alaimo and H.E. Russell, J. Med. Chem., 15, 335 (1972); https://doi.org/10.1021/jm00273a034
- Q. Li, L.A. Mitscher and L.L. Shen, Med. Res. Rev., 20, 231 (2000); https://doi.org/10.1002/1098-1128(200007)20:4<231::AIDMED1>3.0.CO;2-N
- G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor and M.L. Brown, J. Med. Chem., 51, 4620 (2008); https://doi.org/10.1021/jm800271c
- E.M. Berman and L.M. Werbel, J. Med. Chem., 34, 479 (1991); https://doi.org/10.1021/jm00106a001
- R.J. Cox and D. O’Hagan, J. Chem. Soc., Perkin Trans. I, 2537 (1991); https://doi.org/10.1039/p19910002537
- J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M.L. Vericat, L. Conte, J. Ramis, M. Merlos, J. García-Rafanell and J. Forn, J. Med. Chem., 41, 1869 (1998); https://doi.org/10.1021/jm9707277
- M. Nagarajan, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier and M. Cushman, J. Med. Chem., 46, 5712 (2003); https://doi.org/10.1021/jm030313f
- L.A. Hasvold, W. Wang, S.L. Gwaltney II, T.W. Rockway, L.T.J. Nelson, R.A. Mantei, S.A. Fakhoury, G.M. Sullivan, Q. Li, N.H. Lin, L. Wang, H.Y. Zhang, J. Cohen, W.Z. Gu, K. Marsh, J. Bauch, S. Rosenberg and H.L. Sham, Bioorg. Med. Chem. Lett., 13, 4001 (2003); https://doi.org/10.1016/j.bmcl.2003.08.058
- Archana, V.K. Srivastava and A. Kumar, Eur. J. Med. Chem., 37, 873 (2002); https://doi.org/10.1016/S0223-5234(02)01389-2
- O.I. El-Sabbagh, S.M. Ibrahim, M.M. Baraka and H. Kothayer, Arch. Pharm. Chem. Life Sci., 343, 274 (2010).
- V.J. Ram, Farhanullah, B.K. Tripathi and A.K. Srivastava, Bioorg. Med. Chem., 11, 2439 (2003); https://doi.org/10.1016/S0968-0896(03)00142-1
- J.I. Levin, P.S. Chan, T. Bailey, A.S. Katocs Jr. and A.M. Venkatesan, Bioorg. Med. Chem. Lett., 4, 1141 (1994); https://doi.org/10.1016/S0960-894X(01)80244-4
- J. Rudolph, W.P. Esler, S. O’Connor, P.D.G. Coish, P.L. Wickens, M. Brands, D.E. Bierer, B.T. Bloomquist, G. Bondar, L. Chen, C.Y. Chuang, T.H. Claus, Z. Fathi, W. Fu, U.R. Khire, J.A. Kristie, X.G. Liu, D.B. Lowe, A.C. Mcclure, M. Michels, A.A. Ortiz, P.D. Ramsden, R.W. Schoenleber, T.E. Shelekhin, A. Vakalopoulos, W.F. Tang, L. Wang, L. Yi, S.J. Gardell, J.N. Livingston, L.J. Sweet and W.H. Bullock, J. Med. Chem., 50, 5202 (2007); https://doi.org/10.1021/jm070071+
- A. Davoodnia, M. Khashi and N. Tavakoli-Hoseini, Chin. J. Catal., 35, 1054 (2014); https://doi.org/10.1016/S1872-2067(14)60041-3
- H.R. Shaterian and F. Rigi, Res. Chem. Intermed., 41, 721 (2015); https://doi.org/10.1007/s11164-013-1223-z
- M. Ghashang, Orient. J. Chem., 28, 1213 (2012); https://doi.org/10.13005/ojc/280317
- G. Majid, A. Kobra, M.-P. Hamed and S.H. Reza, Chin. J. Chem., 29, 1617 (2011); https://doi.org/10.1002/cjoc.201180290
- M.Z. Kassaee, S. Rostamizadeh, N. Shadjou, E. Motamedi and M. Esmaeelzadeh, J. Heterocycl. Chem., 47, 1421 (2010); https://doi.org/10.1002/jhet.506
- J. Safari and S. Gandomi-Ravandi, J. Mol. Catal. Chem., 390, 1 (2014); https://doi.org/10.1016/j.molcata.2014.02.013
- M.P. Surpur, P.R. Singh, S.B. Patil and S.D. Samant, Synth. Commun., 37, 1965 (2007); https://doi.org/10.1080/00397910701354699
- A. Shokrolahi, A. Zali, M.A. Zare and K. Esmaeilpour, Iran. J. Catal., 2, 91 (2012).
- P. Sivaguru, K. Parameswaran, M. Kiruthiga, P. Vadivel and A. Lalitha, J. Iran. Chem. Soc., 12, 95 (2015); https://doi.org/10.1007/s13738-014-0459-x
- Z. Karimi-Jaberi and L. Zarei, Acta Chim. Slov., 60, 178 (2013).
- G. Yassaghi, A. Davoodnia, S. Allameh, A. Zare-Bidaki and N. TavakoliHoseini, Bull. Korean Chem. Soc., 33, 2724 (2012); https://doi.org/10.5012/bkcs.2012.33.8.2724
- A. Rostami and A. Tavakoli, Chin. Chem. Lett., 22, 1317 (2011); https://doi.org/10.1016/j.cclet.2011.06.008
- J. Wang, Y. Zong, R. Fu, Y. Niu, G. Yue, Z. Quan, X. Wang, Y. Pan, Ultrason. Sonochem., 21, 29 (2014); https://doi.org/10.1016/j.ultsonch.2013.05.009
- R.Z. Qiao, B.L. Xu and Y.H. Wang, Chin. Chem. Lett., 18, 656 (2007); https://doi.org/10.1016/j.cclet.2007.04.036
- A. Rostami, B. Tahmasbi, H. Gholami and H. Taymorian, Chin. Chem. Lett., 24, 211 (2013); https://doi.org/10.1016/j.cclet.2013.01.032
- K. Ramesh, K. Karnakar, G. Satish, B.S.P. Anil Kumar and Y.V.D. Nageswar, Tetrahedron Lett., 53, 6936 (2012); https://doi.org/10.1016/j.tetlet.2012.10.029
- Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang and Y. Pan, Chin. Chem. Lett., 21, 778 (2010); https://doi.org/10.1016/j.cclet.2010.03.022
- 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
- M. Abdollahi-Alibeik and E. Shabani, Chin. Chem. Lett., 22, 1163 (2011); https://doi.org/10.1016/j.cclet.2011.05.011
- B.A. Dar, A.K. Sahu, P. Patidar, P.R. Sharma, N. Mupparapu, D. Vyas, S. Maity, M. Sharma and B. Singh, J. Ind. Eng. Chem., 19, 407 (2013); https://doi.org/10.1016/j.jiec.2012.08.027
- H.R. Shaterian, A.R. Oveisi and M. Honarmand, Synth. Commun., 40, 1231 (2010); https://doi.org/10.1080/00397910903064831
- R. Katla, R. Chowrasia, C.D.G. Da Silva, A.R. De Oliveira, B.F. Dos Santos and N.L.C. Domingues, Synth., 49, 5143 (2017); https://doi.org/10.1055/s-0036-1590886
- S.J. Wu, Z.Q. Zhao, J.S. Gao, B.H. Chen and G.F. Chen, Res. Chem. Intermed., 45, 2327 (2019); https://doi.org/10.1007/s11164-018-03732-w
References
M.R. Yadav, S.T. Shirude, A. Parmar, R. Balaraman and R. Giridhar, Chem. Heterocycl. Compd., 42, 1038 (2006); https://doi.org/10.1007/s10593-006-0201-4
R.J. Alaimo and H.E. Russell, J. Med. Chem., 15, 335 (1972); https://doi.org/10.1021/jm00273a034
Q. Li, L.A. Mitscher and L.L. Shen, Med. Res. Rev., 20, 231 (2000); https://doi.org/10.1002/1098-1128(200007)20:4<231::AIDMED1>3.0.CO;2-N
G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor and M.L. Brown, J. Med. Chem., 51, 4620 (2008); https://doi.org/10.1021/jm800271c
E.M. Berman and L.M. Werbel, J. Med. Chem., 34, 479 (1991); https://doi.org/10.1021/jm00106a001
R.J. Cox and D. O’Hagan, J. Chem. Soc., Perkin Trans. I, 2537 (1991); https://doi.org/10.1039/p19910002537
J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M.L. Vericat, L. Conte, J. Ramis, M. Merlos, J. García-Rafanell and J. Forn, J. Med. Chem., 41, 1869 (1998); https://doi.org/10.1021/jm9707277
M. Nagarajan, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier and M. Cushman, J. Med. Chem., 46, 5712 (2003); https://doi.org/10.1021/jm030313f
L.A. Hasvold, W. Wang, S.L. Gwaltney II, T.W. Rockway, L.T.J. Nelson, R.A. Mantei, S.A. Fakhoury, G.M. Sullivan, Q. Li, N.H. Lin, L. Wang, H.Y. Zhang, J. Cohen, W.Z. Gu, K. Marsh, J. Bauch, S. Rosenberg and H.L. Sham, Bioorg. Med. Chem. Lett., 13, 4001 (2003); https://doi.org/10.1016/j.bmcl.2003.08.058
Archana, V.K. Srivastava and A. Kumar, Eur. J. Med. Chem., 37, 873 (2002); https://doi.org/10.1016/S0223-5234(02)01389-2
O.I. El-Sabbagh, S.M. Ibrahim, M.M. Baraka and H. Kothayer, Arch. Pharm. Chem. Life Sci., 343, 274 (2010).
V.J. Ram, Farhanullah, B.K. Tripathi and A.K. Srivastava, Bioorg. Med. Chem., 11, 2439 (2003); https://doi.org/10.1016/S0968-0896(03)00142-1
J.I. Levin, P.S. Chan, T. Bailey, A.S. Katocs Jr. and A.M. Venkatesan, Bioorg. Med. Chem. Lett., 4, 1141 (1994); https://doi.org/10.1016/S0960-894X(01)80244-4
J. Rudolph, W.P. Esler, S. O’Connor, P.D.G. Coish, P.L. Wickens, M. Brands, D.E. Bierer, B.T. Bloomquist, G. Bondar, L. Chen, C.Y. Chuang, T.H. Claus, Z. Fathi, W. Fu, U.R. Khire, J.A. Kristie, X.G. Liu, D.B. Lowe, A.C. Mcclure, M. Michels, A.A. Ortiz, P.D. Ramsden, R.W. Schoenleber, T.E. Shelekhin, A. Vakalopoulos, W.F. Tang, L. Wang, L. Yi, S.J. Gardell, J.N. Livingston, L.J. Sweet and W.H. Bullock, J. Med. Chem., 50, 5202 (2007); https://doi.org/10.1021/jm070071+
A. Davoodnia, M. Khashi and N. Tavakoli-Hoseini, Chin. J. Catal., 35, 1054 (2014); https://doi.org/10.1016/S1872-2067(14)60041-3
H.R. Shaterian and F. Rigi, Res. Chem. Intermed., 41, 721 (2015); https://doi.org/10.1007/s11164-013-1223-z
M. Ghashang, Orient. J. Chem., 28, 1213 (2012); https://doi.org/10.13005/ojc/280317
G. Majid, A. Kobra, M.-P. Hamed and S.H. Reza, Chin. J. Chem., 29, 1617 (2011); https://doi.org/10.1002/cjoc.201180290
M.Z. Kassaee, S. Rostamizadeh, N. Shadjou, E. Motamedi and M. Esmaeelzadeh, J. Heterocycl. Chem., 47, 1421 (2010); https://doi.org/10.1002/jhet.506
J. Safari and S. Gandomi-Ravandi, J. Mol. Catal. Chem., 390, 1 (2014); https://doi.org/10.1016/j.molcata.2014.02.013
M.P. Surpur, P.R. Singh, S.B. Patil and S.D. Samant, Synth. Commun., 37, 1965 (2007); https://doi.org/10.1080/00397910701354699
A. Shokrolahi, A. Zali, M.A. Zare and K. Esmaeilpour, Iran. J. Catal., 2, 91 (2012).
P. Sivaguru, K. Parameswaran, M. Kiruthiga, P. Vadivel and A. Lalitha, J. Iran. Chem. Soc., 12, 95 (2015); https://doi.org/10.1007/s13738-014-0459-x
Z. Karimi-Jaberi and L. Zarei, Acta Chim. Slov., 60, 178 (2013).
G. Yassaghi, A. Davoodnia, S. Allameh, A. Zare-Bidaki and N. TavakoliHoseini, Bull. Korean Chem. Soc., 33, 2724 (2012); https://doi.org/10.5012/bkcs.2012.33.8.2724
A. Rostami and A. Tavakoli, Chin. Chem. Lett., 22, 1317 (2011); https://doi.org/10.1016/j.cclet.2011.06.008
J. Wang, Y. Zong, R. Fu, Y. Niu, G. Yue, Z. Quan, X. Wang, Y. Pan, Ultrason. Sonochem., 21, 29 (2014); https://doi.org/10.1016/j.ultsonch.2013.05.009
R.Z. Qiao, B.L. Xu and Y.H. Wang, Chin. Chem. Lett., 18, 656 (2007); https://doi.org/10.1016/j.cclet.2007.04.036
A. Rostami, B. Tahmasbi, H. Gholami and H. Taymorian, Chin. Chem. Lett., 24, 211 (2013); https://doi.org/10.1016/j.cclet.2013.01.032
K. Ramesh, K. Karnakar, G. Satish, B.S.P. Anil Kumar and Y.V.D. Nageswar, Tetrahedron Lett., 53, 6936 (2012); https://doi.org/10.1016/j.tetlet.2012.10.029
Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang and Y. Pan, Chin. Chem. Lett., 21, 778 (2010); https://doi.org/10.1016/j.cclet.2010.03.022
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
M. Abdollahi-Alibeik and E. Shabani, Chin. Chem. Lett., 22, 1163 (2011); https://doi.org/10.1016/j.cclet.2011.05.011
B.A. Dar, A.K. Sahu, P. Patidar, P.R. Sharma, N. Mupparapu, D. Vyas, S. Maity, M. Sharma and B. Singh, J. Ind. Eng. Chem., 19, 407 (2013); https://doi.org/10.1016/j.jiec.2012.08.027
H.R. Shaterian, A.R. Oveisi and M. Honarmand, Synth. Commun., 40, 1231 (2010); https://doi.org/10.1080/00397910903064831
R. Katla, R. Chowrasia, C.D.G. Da Silva, A.R. De Oliveira, B.F. Dos Santos and N.L.C. Domingues, Synth., 49, 5143 (2017); https://doi.org/10.1055/s-0036-1590886
S.J. Wu, Z.Q. Zhao, J.S. Gao, B.H. Chen and G.F. Chen, Res. Chem. Intermed., 45, 2327 (2019); https://doi.org/10.1007/s11164-018-03732-w