Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Acid Catalyzed Multicomponent One-Pot Synthesis of New Quinazolinone based Unsymmetrical C-N Linked Bis Heterocycles
Corresponding Author(s) : A.K.D. Bhavani
Asian Journal of Chemistry,
Vol. 34 No. 2 (2022): Vol 34 Issue 2
Abstract
A novel series of unsymmetrical C-N linked bis heterocycles bearing quinazolinone and acridinedione skeletons have been synthesized in an acid promoted one pot multicomponent reaction. A blend of 6-aminoquinazolin-4-(3H)-one, aromatic aldehydes and cyclohexane-1,3-dione in a simple and efficient condensation-cyclization reaction using hydrochloric acid in catalytic amount as catalyst afforded unsymmetrical bis hybrids in good to excellent yields. Multiheterocyclic hybrid compounds were also synthesized using heterocyclic ring containing aldehyde in three component reaction. The synthesized quinazolinone-acridindione hybrids were characterized using spectroscopic techniques such as a IR, 1H NMR, 13C NMR, ESI-mass and HRMS.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- A.A. Radwan, F.K. Alanazi and A. Al-Dhfyan, Drug Res., 63, 129 (2013); https://doi.org/10.1055/s-0032-1333306
- R. Karan, P. Agarwal, M. Sinha and N. Mahato, ChemEngineering, 5, 73 (2021); https://doi.org/10.3390/chemengineering5040073
- I. Khan, S. Zaib, S. Batool, N. Abbas, Z. Ashraf, J. Iqbal and A. Saeed, Bioorg. Med. Chem., 24, 2361 (2016); https://doi.org/10.1016/j.bmc.2016.03.031
- M.M. Ghorab, Z.H. Ismail, A.A. Radwan and M. Abdalla, Acta Pharm., 63, 1 (2013); https://doi.org/10.2478/acph-2013-0006
- J.S. Negi, A.S. Bisht and D.K. Sharma, Indian J. Pharm. Chem. Anal., 7, 61 (2020); https://doi.org/10.18231/j.ijpca.2020.009
- N. Gokhan-Kelekci, S. Koyunoglu, S. Yabanoglu, K. Yelekci, O. Ozgen, G. Ucar, K. Erol, E. Kendi and A. Yesilada, Bioorg. Med. Chem., 17, 675 (2009); https://doi.org/10.1016/j.bmc.2008.11.068
- A. Yesilada, S. Koyunoglu, N. Saygilia, E. Kupeli, E. Yesilada, E. Bedir and I. Khanc, Arch. Pharm., 337, 96 (2004); https://doi.org/10.1002/ardp.200200752
- F.A.M. Al-Omary, G.S. Hassan, S.M. El-Messery, M.N. Nagi, E.-S.E. Habib and H.I. El-Subbagh, Eur. J. Med. Chem., 63, 33 (2013); https://doi.org/10.1016/j.ejmech.2012.12.061
- H. Panwar, S. Singh, A. Kumar, S. Singh, N. Singh and H. Singh, Der Pharma Chem., 3, 399 (2011).
- P.S.N. Reddy, P.P. Reddy and T. Vasantha, Indian J. Chem., 41B, 1946 (2002).
- D.P. Jindal, R.S. Bhatti, S. Ahlawat and R. Gupta, Eur. J. Med. Chem., 37, 419 (2002); https://doi.org/10.1016/S0223-5234(02)01345-4
- A. Banerjee, M.Y. Pawar, S. Patil, P.S. Yadav, P.A. Kadam, V.G. Kattige, D.S. Deshpande, P.V. Pednekar, M.K. Pisat and L.A. Gharat, Bioorg. Med. Chem. Lett., 24, 4838 (2014); https://doi.org/10.1016/j.bmcl.2014.08.056
- Z. Kilic-Kurt, F. Bakar and S. Olgen, Arch. Pharm., 348, 715 (2015); https://doi.org/10.1002/ardp.201500109
- A. Naouri, A. Djemoui, M.R. Ouahrani, M.B. Lahrech, N. Lemouari, D.H.A. Rocha, H. Albuquerque, R.F. Mendes, F.A. Almeida Paz, L.A. Helguero, K. Bachari, O. Talhi and A.M.S. Silva, J. Mol. Struct., 1217, 128325 (2020); https://doi.org/10.1016/j.molstruc.2020.128325
- J.S. Rupar, V.D. Dobricic, M.M. Aleksic, J.S. Brboric and O.A. Cudina, Kragujevac J. Sci., 40, 83 (2018).
- N.P. Singh, R. Kumar, D.N. Pra, S. Sharma and O. Silakari, Int. J. Biol.
- Chem., 5, 193 (2011); https://doi.org/10.3923/ijbc.2011.193.199
- S.M. Sondhi, J. Singh, R. Rani, P.P. Gupta, S.K. Agrawal and A.K. Saxena, Eur. J. Med. Chem., 45, 555 (2010); https://doi.org/10.1016/j.ejmech.2009.10.042
- M.S. Baseer, G.K. Shankaraiah, V.M. Atul, G.M. Gajanan, S.C. Santosh and S.D. Bhaskar, Der Pharma. Chem., 4, 25 (2010).
- D.G. Carole, D.M. Michel, C. Julien, D. Florence, N. Anna, J. Séverine, D. Gérard, T.-D. Pierre and G. Jean-Pierre, Bioorg. Med. Chem., 13, 5560 (2005); https://doi.org/10.1016/j.bmc.2005.06.045
- A. Srivastava and Nizamuddin, Indian J. Heterocycl. Chem., 13, 261 (2004).
- S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfart, J. Molnar and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); https://doi.org/10.1016/S0223-5234(02)01422-8
- S.A. Moallem, N. Dehghani, S. Mehri, S. Shahsavand, M. Alibolandi and F. Hadizadeh, Res. Pharm. Sci., 10, 214 (2015).
- S. Balalaie, F. Chadegani, F. Darviche and H.R. Bijanzadeh, Chin. J. Chem., 27, 1953 (2009); https://doi.org/10.1002/cjoc.200990328
- L.-B. Li, S.-J. Ji and Y. Liu, Chin. J. Chem., 26, 979 (2008); https://doi.org/10.1002/cjoc.200890208
- F.-M. Wang, L. Zhou, J.-F. Li, D. Bao and L.-Z. Chen, J. Heterocycl. Chem., 54, 3120 (2017); https://doi.org/10.1002/jhet.2925
- K. Venkatesan, S.S. Pujari and K.V. Srinivasan, Synth. Commun., 39, 228 (2008); https://doi.org/10.1080/00397910802044306
- A. Davoodnia, A. Khojastehnezhad and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 656 (2011); https://doi.org/10.5012/bkcs.2011.32.2.656
- M. Kidwai and D. Bhatnagar, Tetrahedron Lett., 51, 2700 (2010); https://doi.org/10.1016/j.tetlet.2010.03.033
- T.-S. Jin, J.-S. Zhang, T.-T. Guo, A.-Q. Wang and T.-S. Li, Synthesis, 2001 (2004); https://doi.org/10.1055/s-2004-829151
- N. Jazi, S. Fozooni and H. Hamidian, J. Chem. Res., 42, 80 (2018); https://doi.org/10.3184/174751918X15181752711035
- X.-S. Wang, M.-M. Zhang, D.-Q. Shi, S.-J. Tu, X.-Y. Wei and Z.-M. Zong, J. Chem. Res., 719 (2006); https://doi.org/10.3184/030823406779173352
- Q.H. To, Y.-R. Lee and S.-H. Kim, Bull. Korean Chem. Soc., 33, 1170 (2012); https://doi.org/10.5012/bkcs.2012.33.4.1170
- M.A. Pasha, R.-u.-R. Khan and K.B. Ramesh, Can. Chem. Trans., 4, 90 (2016).
- S. Chandrasekhar, Y. Srinivasa Rao, L. Sreelakshmi, B. Mahipal and C. Raji Reddy, Synthesis, 1737 (2008); https://doi.org/10.1055/s-2008-1067039
- A. Khazaei, A.R. Moosavi-Zare, Z. Mohammadi, V. Khakyzadeh and J. Afsar, J. Chin. Chem. Soc., 63, 165 (2016); https://doi.org/10.1002/jccs.201500384
- H. Alinezhad and S.M. Tavakkoli, Scient. World J., 2013, 575636 (2013); https://doi.org/10.1155/2013/575636
- G.M. Ziarani, A. Badiei, M. Hassanzadeh and S. Mousavi, Arab. J. Chem., 7, 335 (2014); https://doi.org/10.1016/j.arabjc.2011.01.037
- J.N. Sangshetti, P.P. Dharmadhikari, R.S. Chouthe and B. Fatema, Arab. J. Chem., 10, S10 (2017); https://doi.org/10.1016/j.arabjc.2012.06.005
- M. Nasr-Esfahani, Z. Rafiee and H. Kashi, J. Iran. Chem. Soc., 13, 1449 (2016); https://doi.org/10.1007/s13738-016-0860-8
- W. Shen, L.-M. Wang, H. Tian, J. Tang and J. Yu, J. Fluor. Chem., 130, 522 (2009); https://doi.org/10.1016/j.jfluchem.2009.02.014
- D. Kour, D.R. Patil, M.B. Deshmukh, V.K. Gupta and R. Kant, Eur. Chem. Bull., 3, 173 (2014).
- R. Vaid, M. Gupta and V.K. Gupta, J. Iran. Chem. Soc., 14, 2199 (2017); https://doi.org/10.1007/s13738-017-1156-3
- N. Biswas and D. Srimani, J. Org. Chem., 86, 9733 (2021); https://doi.org/10.1021/acs.joc.1c01075
- L.H.R. Alponti, M. Picinini, E.A. Urquieta-Gonzalez and A.G. Corrêa, J. Mol. Struct., 1227, 129430 (2021); https://doi.org/10.1016/j.molstruc.2020.129430
- A. Dorehgiraee, E. Tavakolinejad Kermani and H. Khabazzadeh, J. Chem. Sci., 126, 1039 (2014); https://doi.org/10.1007/s12039-014-0628-6
- P. Shankaraiah, A.K.D. Bhavani, A.K. Kumar and K. Ramakrishna, Russ. J. Gen. Chem., 90, 720 (2020); https://doi.org/10.1134/S1070363220040246
References
A.A. Radwan, F.K. Alanazi and A. Al-Dhfyan, Drug Res., 63, 129 (2013); https://doi.org/10.1055/s-0032-1333306
R. Karan, P. Agarwal, M. Sinha and N. Mahato, ChemEngineering, 5, 73 (2021); https://doi.org/10.3390/chemengineering5040073
I. Khan, S. Zaib, S. Batool, N. Abbas, Z. Ashraf, J. Iqbal and A. Saeed, Bioorg. Med. Chem., 24, 2361 (2016); https://doi.org/10.1016/j.bmc.2016.03.031
M.M. Ghorab, Z.H. Ismail, A.A. Radwan and M. Abdalla, Acta Pharm., 63, 1 (2013); https://doi.org/10.2478/acph-2013-0006
J.S. Negi, A.S. Bisht and D.K. Sharma, Indian J. Pharm. Chem. Anal., 7, 61 (2020); https://doi.org/10.18231/j.ijpca.2020.009
N. Gokhan-Kelekci, S. Koyunoglu, S. Yabanoglu, K. Yelekci, O. Ozgen, G. Ucar, K. Erol, E. Kendi and A. Yesilada, Bioorg. Med. Chem., 17, 675 (2009); https://doi.org/10.1016/j.bmc.2008.11.068
A. Yesilada, S. Koyunoglu, N. Saygilia, E. Kupeli, E. Yesilada, E. Bedir and I. Khanc, Arch. Pharm., 337, 96 (2004); https://doi.org/10.1002/ardp.200200752
F.A.M. Al-Omary, G.S. Hassan, S.M. El-Messery, M.N. Nagi, E.-S.E. Habib and H.I. El-Subbagh, Eur. J. Med. Chem., 63, 33 (2013); https://doi.org/10.1016/j.ejmech.2012.12.061
H. Panwar, S. Singh, A. Kumar, S. Singh, N. Singh and H. Singh, Der Pharma Chem., 3, 399 (2011).
P.S.N. Reddy, P.P. Reddy and T. Vasantha, Indian J. Chem., 41B, 1946 (2002).
D.P. Jindal, R.S. Bhatti, S. Ahlawat and R. Gupta, Eur. J. Med. Chem., 37, 419 (2002); https://doi.org/10.1016/S0223-5234(02)01345-4
A. Banerjee, M.Y. Pawar, S. Patil, P.S. Yadav, P.A. Kadam, V.G. Kattige, D.S. Deshpande, P.V. Pednekar, M.K. Pisat and L.A. Gharat, Bioorg. Med. Chem. Lett., 24, 4838 (2014); https://doi.org/10.1016/j.bmcl.2014.08.056
Z. Kilic-Kurt, F. Bakar and S. Olgen, Arch. Pharm., 348, 715 (2015); https://doi.org/10.1002/ardp.201500109
A. Naouri, A. Djemoui, M.R. Ouahrani, M.B. Lahrech, N. Lemouari, D.H.A. Rocha, H. Albuquerque, R.F. Mendes, F.A. Almeida Paz, L.A. Helguero, K. Bachari, O. Talhi and A.M.S. Silva, J. Mol. Struct., 1217, 128325 (2020); https://doi.org/10.1016/j.molstruc.2020.128325
J.S. Rupar, V.D. Dobricic, M.M. Aleksic, J.S. Brboric and O.A. Cudina, Kragujevac J. Sci., 40, 83 (2018).
N.P. Singh, R. Kumar, D.N. Pra, S. Sharma and O. Silakari, Int. J. Biol.
Chem., 5, 193 (2011); https://doi.org/10.3923/ijbc.2011.193.199
S.M. Sondhi, J. Singh, R. Rani, P.P. Gupta, S.K. Agrawal and A.K. Saxena, Eur. J. Med. Chem., 45, 555 (2010); https://doi.org/10.1016/j.ejmech.2009.10.042
M.S. Baseer, G.K. Shankaraiah, V.M. Atul, G.M. Gajanan, S.C. Santosh and S.D. Bhaskar, Der Pharma. Chem., 4, 25 (2010).
D.G. Carole, D.M. Michel, C. Julien, D. Florence, N. Anna, J. Séverine, D. Gérard, T.-D. Pierre and G. Jean-Pierre, Bioorg. Med. Chem., 13, 5560 (2005); https://doi.org/10.1016/j.bmc.2005.06.045
A. Srivastava and Nizamuddin, Indian J. Heterocycl. Chem., 13, 261 (2004).
S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfart, J. Molnar and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); https://doi.org/10.1016/S0223-5234(02)01422-8
S.A. Moallem, N. Dehghani, S. Mehri, S. Shahsavand, M. Alibolandi and F. Hadizadeh, Res. Pharm. Sci., 10, 214 (2015).
S. Balalaie, F. Chadegani, F. Darviche and H.R. Bijanzadeh, Chin. J. Chem., 27, 1953 (2009); https://doi.org/10.1002/cjoc.200990328
L.-B. Li, S.-J. Ji and Y. Liu, Chin. J. Chem., 26, 979 (2008); https://doi.org/10.1002/cjoc.200890208
F.-M. Wang, L. Zhou, J.-F. Li, D. Bao and L.-Z. Chen, J. Heterocycl. Chem., 54, 3120 (2017); https://doi.org/10.1002/jhet.2925
K. Venkatesan, S.S. Pujari and K.V. Srinivasan, Synth. Commun., 39, 228 (2008); https://doi.org/10.1080/00397910802044306
A. Davoodnia, A. Khojastehnezhad and N. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 32, 656 (2011); https://doi.org/10.5012/bkcs.2011.32.2.656
M. Kidwai and D. Bhatnagar, Tetrahedron Lett., 51, 2700 (2010); https://doi.org/10.1016/j.tetlet.2010.03.033
T.-S. Jin, J.-S. Zhang, T.-T. Guo, A.-Q. Wang and T.-S. Li, Synthesis, 2001 (2004); https://doi.org/10.1055/s-2004-829151
N. Jazi, S. Fozooni and H. Hamidian, J. Chem. Res., 42, 80 (2018); https://doi.org/10.3184/174751918X15181752711035
X.-S. Wang, M.-M. Zhang, D.-Q. Shi, S.-J. Tu, X.-Y. Wei and Z.-M. Zong, J. Chem. Res., 719 (2006); https://doi.org/10.3184/030823406779173352
Q.H. To, Y.-R. Lee and S.-H. Kim, Bull. Korean Chem. Soc., 33, 1170 (2012); https://doi.org/10.5012/bkcs.2012.33.4.1170
M.A. Pasha, R.-u.-R. Khan and K.B. Ramesh, Can. Chem. Trans., 4, 90 (2016).
S. Chandrasekhar, Y. Srinivasa Rao, L. Sreelakshmi, B. Mahipal and C. Raji Reddy, Synthesis, 1737 (2008); https://doi.org/10.1055/s-2008-1067039
A. Khazaei, A.R. Moosavi-Zare, Z. Mohammadi, V. Khakyzadeh and J. Afsar, J. Chin. Chem. Soc., 63, 165 (2016); https://doi.org/10.1002/jccs.201500384
H. Alinezhad and S.M. Tavakkoli, Scient. World J., 2013, 575636 (2013); https://doi.org/10.1155/2013/575636
G.M. Ziarani, A. Badiei, M. Hassanzadeh and S. Mousavi, Arab. J. Chem., 7, 335 (2014); https://doi.org/10.1016/j.arabjc.2011.01.037
J.N. Sangshetti, P.P. Dharmadhikari, R.S. Chouthe and B. Fatema, Arab. J. Chem., 10, S10 (2017); https://doi.org/10.1016/j.arabjc.2012.06.005
M. Nasr-Esfahani, Z. Rafiee and H. Kashi, J. Iran. Chem. Soc., 13, 1449 (2016); https://doi.org/10.1007/s13738-016-0860-8
W. Shen, L.-M. Wang, H. Tian, J. Tang and J. Yu, J. Fluor. Chem., 130, 522 (2009); https://doi.org/10.1016/j.jfluchem.2009.02.014
D. Kour, D.R. Patil, M.B. Deshmukh, V.K. Gupta and R. Kant, Eur. Chem. Bull., 3, 173 (2014).
R. Vaid, M. Gupta and V.K. Gupta, J. Iran. Chem. Soc., 14, 2199 (2017); https://doi.org/10.1007/s13738-017-1156-3
N. Biswas and D. Srimani, J. Org. Chem., 86, 9733 (2021); https://doi.org/10.1021/acs.joc.1c01075
L.H.R. Alponti, M. Picinini, E.A. Urquieta-Gonzalez and A.G. Corrêa, J. Mol. Struct., 1227, 129430 (2021); https://doi.org/10.1016/j.molstruc.2020.129430
A. Dorehgiraee, E. Tavakolinejad Kermani and H. Khabazzadeh, J. Chem. Sci., 126, 1039 (2014); https://doi.org/10.1007/s12039-014-0628-6
P. Shankaraiah, A.K.D. Bhavani, A.K. Kumar and K. Ramakrishna, Russ. J. Gen. Chem., 90, 720 (2020); https://doi.org/10.1134/S1070363220040246