Abstract
In this study, several new 12-aryl/heteroaryl-3,3-dimethyl-tetrahydrobenzo[b]acridine-1,6,11(2H)-trione heterocyclic compounds that can be considered as 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones, have been synthesized through the three-component cyclocondensation of benzaldehydes/heteroaldehydes, 2-amino-1,4-naphthoquinone, and dimedone. The pot-, atom-, and step-economy reactions were implemented under reflux conditions. One of the most important aspects of this reaction is the use of ethanol as the reaction medium taking into account the principles of green chemistry. Not using a catalyst in this type of reactions is also significant from the standpoint of green chemistry. The protocol developed in this study has the benefits of the simplicity, no use of chromatographic methods for purification, structural diversity, employing non-toxic solvent, good-to-high yields, safety, and using cost-effective solvent. The structures of the newly synthesized 1,4-naphthoquinone fused with 4-substituted 7,7-dimethyl-4,6,7,8-tetrahydroquinolin-5(1H)-ones were confirmed employing spectroscopic data as well as elemental analysis.
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J.F.A. Filho, B.C. Lemos, A.S. de Souza, S. Pinheiro, S.J. Greco, Tetrahedron 73, 6977 (2017)
I. Khan, A. Ibrar, N. Abbas, A. Saeed, Res. Chem. Intermed. 42, 5147 (2016)
S. Das, A.K. Bagdi, S. Santra, A. Majee, A. Hajra, Res. Chem. Intermed. 41, 6749 (2015)
R. Jiang, M. Liu, H. Huang, L. Mao, Q. Huang, Y. Wen, Q.Y. Cao, J. Tian, X. Zhang, Y. Wei, J. Colloid Interface Sci. 519, 137 (2018)
M.R. Bhosle, D. Nipte, J. Gaikwad, M.A. Shaikh, G.M. Bondle, J.N. Sangshetti, Res. Chem. Intermed. 44, 7047 (2018)
P. Mane, B. Shinde, P. Mundada, V. Gawade, B. Karale, A. Burungale, Res. Chem. Intermed. (2019). https://doi.org/10.1007/s11164-019-03945-7
C. Lambruschini, A. Basso, L. Banf, Drug Discov. Today Technol. 29, 3 (2018)
S. Saranya, K.R. Rohit, S. Radhika, G. Anilkumar, Org. Biomol. Chem. 17, 8048 (2019)
S. Zhi, X. Ma, W. Zhang, Org. Biomol. Chem. 17, 7632 (2019)
A. Al Otaibi, F.M. Deane, C.C. Russell, L. Hizartzidis, S.N. McCluskey, J.A. Sakoff, A. McCluskey, RSC Adv. 9, 7652 (2019)
M. de Souza Siqueira, L.C. da Silva-Filho, Tetrahedron Lett. 57, 5050 (2016)
N.G. Salunkhe, C.A. Ladole, N.V. Thakare, A.S. Aswar, Res. Chem. Intermed. 44, 355 (2018)
C. Altuğ, L.Y. Saleh, E. Caner, H. Güneş, M. Sameeullah, Phosphorus Sulfur Silicon Relat. Elem. 194, 111 (2019)
M.R. Bhosle, M.A. Shaikh, D. Nipate, L.D. Khillare, G.M. Bondle, J.N. Sangshetti, Polycycl. Aromat. Compd. (2019). https://doi.org/10.1080/10406638.2018.1533875
C.C. Jiao, Y.C. Tian, H.L. Cong, Y.Q. Shen, B. Yu, Integr. Ferroelectr. 198, 55 (2019)
V. Arandkar, R.R. Vedula, Phosphorus Sulfur Silicon Relat. Elem. 194, 533 (2019)
S.P.N. Sudhan, R. Nasir Ahmed, H. Kiyani, S. Sheik Mansoor, J. Saudi Chem. Soc. 22, 269 (2018)
H. Kiyani, Curr. Org. Synth. 15, 1043 (2018)
H. Kiyani, M. Bamdad, Res. Chem. Intermed. 44, 2761 (2018)
H. Kiyani, A. Mosallanezhad, Curr. Org. Synth. 15, 715 (2018)
A. Jana, P. Bhaumick, A.K. Panday, R. Mishra, L.H. Choudhury, Org. Biomol. Chem. 17, 5316 (2019)
S. Saigal, H. Khan, S. Rahman, M.M. Khan, RSC Adv. 9, 14477 (2019)
T.B. Aquino, J.E.R. do Nascimento, I.F.C. Dias, D.H. de Oliveira, T. Barcellos, E.J. Lenardão, G. Perin, D. Alves, R.G. Jacob, Tetrahedron Lett. 59, 1080 (2018)
A. Malhotra, T. Kaur, R. Bansal, J. Heterocycl. Chem. (2019). https://doi.org/10.1002/jhet.3683
R. Nongrum, G.K. Kharmawlong, J.W.S. Rani, N. Rahman, A. Dutta, R. Nongkhlaw, J. Heterocycl. Chem. (2019). https://doi.org/10.1002/jhet.3680
C. Sambandam, S. Dhanavel, M. Haridoss, G. Mannuthusamy, J. Heterocycl. Chem. (2019). https://doi.org/10.1002/jhet.3656
M.A. Abozeid, M.R. El-Kholany, L.A. Abouzeid, A.R.H. Abdel-Rahman, E.S.I. El-Desoky, J. Heterocycl. Chem. (2019). https://doi.org/10.1002/jhet.3686
N. Aljaar, R. Gujjarappa, M. Al-Refai, M. Shtaiwi, C.C. Malakar, J. Heterocycl. Chem. (2019). https://doi.org/10.1002/jhet.3673
K.M. Sim, P.Q. Chan, X.L. Boo, K.S. Heng, K.W. Lye, K.C. Teo, Lett. Org. Chem. 15, 575 (2018)
A.V. Chate, R.M. Dongre, M.K. Khaire, G.M. Bondle, J.N. Sangshetti, M. Damale, Res. Chem. Intermed. 44, 6119 (2018)
N.A. Akwu, Y. Naidoo, M. Singh, N. Nundkumar, J. Lin, S. Afr, J. Bot. 123, 180 (2019)
B.M. Mbala, J. Jacobs, P. Claes, V. Mudogo, N. De Kimpe, Tetrahedron 67, 8747 (2011)
M.S. Abdelfattah, K. Toume, M.A. Arai, H. Masu, M. Ishibashi, Tetrahedron Lett. 53, 3346 (2012)
E.A. Kolodina, N.I. Lebedeva, M.S. Shvartsberg, Mendeleev Commun. 22, 332 (2012)
J. Wang, W. Li, J. Qin, L. Wang, S. Wei, H. Tang, Bioorg. Chem. 83, 477 (2019)
R. Yang, Y. Chen, L. Pan, Y. Yang, Q. Zheng, Y. Hu, Y. Wang, L. Zhang, Y. Sun, Z. Li, X. Meng, Bioorg. Med. Chem. 26, 4886 (2018)
B. Du, G. Cai, B. Zhao, X. Meng, X. Wang, Y. Li, Res. Chem. Intermed. 39, 1323 (2013)
Y. Li, X. Xu, D. Shi, S. Ji, Chin. J. Chem. 27, 1510 (2009)
W.F. Rabêlo, R. Echemendía, Synth. Commun. 49, 515 (2019)
Z. Gokmen, M.E. Onan, N.G. Deniz, D. Karakas, E. Ulukaya, Synth. Commun. 40, 3008 (2019)
V. Vairaperumal, M. Perumal, P. Sengodu, S. Shanumuganthan, M. Paramasivam, ChemistrySelect 4, 3006 (2019)
X.L. Chen, Y. Dong, S. He, R. Zhang, H. Zhang, L. Tang, K.M. Zhang, J.U. Wang, Synlett 30, 615 (2019)
M. Gholampour, S. Ranjbar, N. Edraki, M. Mohabbati, O. Firuzi, M. Khoshneviszadeh, Bioorg. Chem. 88, 102967 (2019)
A. Kacmaz, Z. Hamurcu, Phosphorus Sulfur Silicon Relat. Element. 193, 831 (2018)
A. Sharma, I.O. Santos, P. Gaur, V.F. Ferreira, C.R.S. Garcia, D.R. da Rocha, Eur. J. Med. Chem. 59, 48 (2013)
S. Ullah, J. Akter, S.J. Kim, J. Yang, Y. Park, P. Chun, H.R. Moon, Med. Chem. Res. 28, 95 (2019)
B.J. Josey, E.S. Inks, X. Wen, C.J. Chou, J. Med. Chem. 56, 1007 (2013)
J. Guo, I.N.C. Kiran, R.S. Reddy, J. Gao, M. Tang, Y. Liu, Y. He, Org. Lett. 18, 2499 (2016)
A. Kosiha, C. Parthiban, K.P. Elango, J. Photochem. Photobiol. B 168, 165 (2017)
A.A. Aly, E.A. Ishak, M.A. Alsharari, N.S. Al-Muaikel, T.M.I. Bedair, J. Heterocycl. Chem. 49, 9 (2012)
W.O. Valenc, T.V. Baiju, F.G. Brito, M.H. Araujo, C. Pessoa, B.C. Cavalcanti, C.A. de Simone, C. Jacob, I.N.N. Namboothiri, E.N. da Silva Junior, ChemistrySelect 2, 4301 (2017)
A.A. Osowole, A.C. Ekennia, O.O. Olubiyi, M. Olagunju, Res. Chem. Intermed. 43, 2565 (2017)
D.Y. Yuk, C.K. Ryu, J.T. Hong, K.H. Chung, W.S. Kang, Y. Kim, H.S. Yoo, M.K. Lee, C.K. Lee, Y.P. Yun, Biochem. Pharmacol. 60, 1001 (2000)
Y.L. Hsu, C.P. Chuang, Synthesis 46, 3374 (2014)
C. Festus, A.C. Ekennia, A.A. Osowole, L.O. Olasunkanmi, D.C. Onwudiwe, O.T. Ujam, Res. Chem. Intermed. 44, 5857 (2018)
A. Kosiha, K.M. Lo, C. Parthiban, K.P. Elango, Mater. Sci. Eng. C 94, 778 (2019)
C. Festus, A.C. Ekennia, C.U. Ibeji, S.N. Okafor, D.C. Onwudiwe, A.A. Osowole, O.T. Ujam, J. Mol. Struct. 1163, 455 (2018)
C. Ibis, Z. Ozsoy-Gunes, A.F. Tuyun, S.S. Ala, H. Bahar, M.V. Stasevych, R.Y. Musyanovych, O. Komarovska-Porokhnyavets, V. Novikov, J. Sulfur Chem. 37, 477 (2016)
J. Li, X. Zhang, H. Xiang, L. Tong, F. Feng, H. Xie, J. Ding, C. Yang, J. Org. Chem. 82, 6795 (2017)
M. Manickam, P.R. Boggu, J. Cho, Y.J. Nam, S.J. Lee, S.H. Jung, Bioorg. Med. Chem. Lett. 28, 2023 (2018)
E.O. Olawode, R. Tandlich, E. Prinsloo, M. Isaacs, H. Hoppe, R. Seldon, D.F. Warner, V. Steenkamp, P.T. Kaye, Bioorg. Med. Chem. Lett. 29, 1572 (2019)
E. Leyva, L.I. Lopez, R.F.G. de la Cruz, C.G. Espinosa-Gonzalez, Res. Chem. Intermed. 43, 1813 (2017)
U. Sharma, D. Katoch, S. Sood, N. Kumar, B. Singh, A. Thakur, A. Gulati, Indian J. Chem. 52B, 1431 (2013)
P. Ravichandiran, S.A. Subramaniyan, S.Y. Kim, J.S. Kim, B.H. Park, K.S. Shim, D.J. Yo, ChemMedChem 14, 532 (2019)
P. Ravichandiran, M. Masłyk, S. Sheet, M. Janeczko, D. Premnath, A.R. Kim, B.H. Park, M.K. Han, D.J. Yoo, ChemistryOpen 8, 589 (2019)
N. Bayrak, H. Yıldırım, A.F. Tuyun, E.M. Kara, B.O. Celik, G.K. Gupta, H.I. Ciftci, M. Fujita, M. Otsuka, H.R. Nasiri, Lett. Drug Des. Discov. 14, 647 (2017)
L.I. Lopez-Lopez, J.J.V. Garcia, A. Saenz-Galindo, S.Y. Silva-Belmares, Lett. Org. Chem. 11, 573 (2014)
S.H. Cardoso, C.R. de Oliveira, A.S. Guimarães, J. Nascimento, J. de Oliveira dos Santos Carmo, J.N. de Souza Ferro, A.C. de Carvalho Correia, E. Barreto, Chem. Biol. Interact. 291, 55 (2018)
A. Murugesan, R.M. Gengan, A. Krishnan, Mater. Chem. Phys. 188, 154 (2017)
G. Mohammadi Ziarani, S. Mousavi, M. Rahimifard, A. Badiei, J. Mex. Chem. Soc. 58, 168 (2014)
S. Janke, S. Boldt, K. Ghazargan, P. Ehlers, A. Villinger, P. Lange, Eur. J. Org. Chem. 2019, 6177 (2019)
F. Shaebani Behbahani, J. Tabeshpour, S. Mirzaei, S. Golmakaniyoon, Z. Tayarani-Najaran, A. Ghasemi, R. Ghodsi, Arch. Pharm. Chem. Life Sci. 352, e1800307 (2019)
I. Antonini, P. Polucci, A. Magnano, S. Martelli, J. Med. Chem. 44, 3329 (2001)
S. Tu, R. Jia, B. Jiang, Y. Zhang, J. Zhang, J. Heterocycl. Chem. 43, 1621 (2006)
T.F. Borgati, J.D. de Souza Filho, A.B. de Oliveira, J. Braz. Chem. Soc. 30, 1138 (2019)
S. Bhand, R. Patil, Y. Shinde, D.N. Lande, S.S. Rao, L. Kathawate, S.P. Gejji, T. Weyhermüller, S. Salunke-Gawali, J. Mol. Struct. 1123, 245 (2016)
J. Mattay, A.G. Griesbeck, Photochemical Key Steps in Organic Synthesis: An Experimental Course Book (Wiley-VCH Verlagsgesellschaft mbH, Weinheim, 1994), p. 105
M. Bayat, F.S. Hosseini, S. Nasri, J. Sulfur Chem. 39, 99 (2018)
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The authors are thankful to Damghan University Research Council for financial support of this study.
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Kamalifar, S., Kiyani, H. An expeditious and green one-pot synthesis of 12-substituted-3,3-dimethyl-3,4,5,12-tetrahydrobenzo[b]acridine-1,6,11(2H)-triones. Res Chem Intermed 45, 5975–5987 (2019). https://doi.org/10.1007/s11164-019-04014-9
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DOI: https://doi.org/10.1007/s11164-019-04014-9