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Research Articles

p-TSA Catalyzed One-Pot Synthesis of 2-(1H-Indol-3-yl)-3-Phenylquinazolin-4(3H)-Ones

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Pages 434-443 | Received 09 Jul 2020, Accepted 29 Nov 2021, Published online: 21 Dec 2021

References

  • R. Rajput, and A. P. Mishra, “A Review on Biological Activity of Quinazolinones,” International Journal of Pharmacy and Pharmaceutical Sciences 4, (2012) : 66–70.
  • J. P. Michael, “Quinoline, Quinazoline and Acridone Alkaloids,”Natural Product Reports 22, no. 5 (2005): 627–46.
  • G. M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor, and M. L. Brown, “Asymmetric Synthesis of 2,3-Dihydro-2-Arylquinazolin-4-Ones: Methodology and Application to a Potent Fluorescent Tubulin Inhibitor with Anticancer Activity,” Journal of Medicinal Chemistry 51, no. 15 (2008): 4620–31.
  • S. B. Mhaske, and N. P. Argade, “The Chemistry of Recently Isolated Naturally Occurring Quinazolinone Alkaloids,”Tetrahedron 62, no. 42 (2006): 9787–826.
  • A. Hameed, M. Al-Rashida, M. Uroos, S. A. Ali, Arshia, M. Ishtiaq, and K. M. Khan, “Quinazoline and Quinazolinone as Important Medicinal Scaffolds: A Comparative Patent Review,” Expert Opinion on Therapeutic Patents 28, no. 4 (2018): 281–97.
  • R. P. Maskey, M. Shaaban, I. Grun-Wollny, and H. Laatsch, “Quinazolin-4-One Derivatives from Streptomyces Isolates,”Journal of Natural Products 67, no. 7 (2004): 1131–4.
  • J. F. Liu, “Rapid Syntheses of Biologically Active Quinazolinone Natural Products Using Microwave Technology,” Current Organic Synthesis 4, no. 2 (2007): 223–37.
  • P. Kundu, A. Mondal, and C. Chowdhury, “A Palladium-Catalyzed Method for the Synthesis of 2-(α-Styryl)-2,3-Dihydroquinazolin-4-Ones and 3-(α-Styryl)-3,4-Dihydro-1,2,4-Benzothiadiazine-1,1-Dioxide: Access to 2-(α-Styryl)Quinazolin-4(3H)-Ones and 3-(α-Styryl)-1,2,4-Benzothiadiazine-1,1-Sioxides,” The Journal of Organic Chemistry 81, no. 15 (2016): 6596–608.
  • S. Li, and J. A. Ma, “ Core-Structure-Inspired Asymmetric Addition Reactions: Enantioselective Synthesis of Dihydrobenzoxazinone- and Dihydroquinazolinone-Based Anti-HIV Agents” Chemical Society Reviews 44, no. 21 (2015): 7439–48.
  • P. Sivaguru, K. Parameswaran, and A. Lalitha, “Antioxidant, Anticancer and Electrochemical Redox Properties of New Bis(2,3-Dihydroquinazolin-4(1H)-One) Derivatives,” Molecular Diversity 21, no. 3 (2017): 611–20.
  • J. Bartroli, E. Turmo, M. Alguero, E. Boncompte, M. L. Vericat, L. Conte, J. Ramis, M. Merlos, J. Garcıa-Rafanell, and J. Forn, “New Azole Antifungals. 3. Synthesis and Antifungal Activity of 3-Substituted-4(3H)-Quinazolinones,” Journal of Medicinal Chemistry 41, no. 11 (1998): 1869–82.
  • R. J. Alaimo, and H. E. Russell, “Antibacterial 2,3-Dihydro-2-(5-Nitro-2-Thienyl)-Quinazolin-4(1H)-Ones,” Journal of Medicinal Chemistry 15, no. 3 (1972): 335–6.
  • E. Cohen, B. Klarberg, and J. R. Vaughan, “Quinazolinone Sulfonamides as Diuretic Agents,” Journal of the American Chemical Society 81, no. 20 (1959): 5508–9.
  • V. Alagarsamy, V. R. Solomon, and M. Murugan, “Synthesis and Pharmacological Investigation of Novel 4-Benzyl-1-Substituted-4H-[1,2,4]Triazolo[4,3-a]Quinazolin-5-Ones as New Class of H1-Antihistaminic Agents,” Bioorganic & Medicinal Chemistry 15, no. 12 (2007): 4009–15.
  • A. Gupta, S. K. Kashaw, N. Jain, H. Rajak, A. Soni, and J. P. Stables, “Design and Synthesis of Some Novel 3-[5-(4-Substituted)phenyl1,3,4-Oxadiazole-2yl]-2-Phenylquinazoline-4(3H)-Ones as Possible Anticonvulsant Agent,” Medicinal Chemistry Research 20, no. 9 (2011): 1638–42.
  • V. Alagarsamy, S. V. Raja, and K. Dhanabal, “Synthesis and Pharmacological Evaluation of Some 3-Phenyl-2-Substituted-3H-Quinazolin-4-One as Analgesic, anti-Inflammatory Agents,” Bioorganic & Medicinal Chemistry 15, no. 1 (2007): 235–41.
  • H. J. Zhang, S. B. Wang, and Z. S. Quan, “Synthesis and Antidepressant Activities of 4-(Substituted-Phenyl)Tetrazolo[1,5-a]Quinazolin-5(4H)-Ones and Their Derivatives,” Molecular Diversity 19, no. 4 (2015): 817–28.
  • Y. Takaya, H. Tasaka, T. Chiba, K. Uwai, M. Tanitsu, H. S. Kim, Y. Wataya, M. Miura, M. Takeshita, and Y. Oshima, “New Type of Febrifugine Analogues, Bearing a Quinolizidine Moiety, Show Potent Antimalarial Activity against Plasmodium Malaria Parasite,” Journal of Medicinal Chemistry 42, no. 16 (1999): 3163–6.
  • W. B. Wright, Jr, A. S. Tomcufcik, P. S. Chan, J. W. Marsico, and J. B. Press, “Thromboxane Synthetase Inhibitors and Antihypertensive Agents. 4. N-[(1H-Imidazol-1-yl)Alkyl] Derivatives of Quinazoline-2,4(1H,3H)-Diones, Quinazolin-4(3H)-Ones, and 1,2,3-Benzotriazin-4(3H)-Ones,” Journal of Medicinal Chemistry 30, no. 12 (1987): 2277–83.
  • Y. S. Sadanadam, R. M. Reddy, and A. Bhaskar, “Synthesis of Substituted 2,3-Dihydro-1-(β-Phenylethyl)-2-Aryl and 2,3-Diaryl-4 (1H)-Quinazolinones and Their Pharmacological Activities,” European Journal of Medicinal Chemistry 22, (1987): 169–73.
  • G. Bonola, R. P. Da, M. J. Magistretti, E. Massarani, and I. Setnikar, “1-Aminoacyl-2,3-Dihydro-4(1H)-Quinazolinone Derivatives with Choleretic and Antifibrillatory Activity,” Journal of Medicinal Chemistry 11, no. 6 (1968): 1136–9.
  • M. S. Manhas, W. A. Hoffman, III, and A. K. Bose, “Heterocyclic Compounds XII. Quinazoline Derivatives as Potential Antifertility Agents,” Journal of Heterocyclic Chemistry 16, no. 4 (1979): 711–5.
  • E. Hamel, C. M. Lin, J. Plowman, H. Wang, K. Lee, and K. D. Paull, “Antitumor 2,3-Dihydro-2- (Aryl)-4(1H)-Quinazolinone Derivatives,” Biochemical Pharmacology 51, no. 1 (1996): 53–9.
  • R. Lakhan, and O. P. Singh, “Syntheses of Some New 4(3H)-Quinazolinones as Potential CNS Active Agents,” Archiv Der Pharmazie 318, no. 3 (1985): 228–38.
  • V. Alagarsamy, and U. S. Pathak, “Synthesis and Antihypertensive Activity of Novel 3-Benzyl-2-Substituted-3H-[1,2,4]Triazolo[5,1-b]Quinazolin-9-Ones,” Bioorganic & Medicinal Chemistry 15, no. 10 (2007): 3457–62.
  • S. Eguchi, “Quinazoline Alkaloids and Related Chemistry,” Topics in Heterocyclic Chemistry 6, (2006): 113–56.
  • R. Mondal, G. Chakraborty, A. K. Guin, S. Pal, and N. D. Paul, “Iron Catalyzed Metal-Ligand Cooperative Approaches towards Sustainable Synthesis of Quinolines and Quinazolin-4(3H)-Ones,” Tetrahedron 100, (2021): 132479.
  • K. El-Adl, A. G. A. El-Helby, R. R. Ayyad, H. A. Mahdy, M. M. Khalifa, H. A. Elnagar, A. B. M. Mehany, A. M. Metwaly, M. A. Elhendawy, M. M. Radwan, et al. “Design, Synthesis, and anti-Proliferative Evaluation of New Quinazolin-4(3H)-Ones as Potential VEGFR-2 Inhibitors,” Bioorganic & Medicinal Chemistry 29, (2021): 115872.
  • A. Faraji, R. Motahari, Z. Hasanvand, T. O. Bakhshaiesh, M. Toolabi, S. Moghimi, L. Firoozpour, M. A. Boshagh, R. Rahmani, S. H. M. E. Ketabforoosh, et al. “Quinazolin-4(3H)-One Based Agents Bearing Thiadiazole-Urea: Synthesis and Evaluation of anti-Proliferative and Antiangiogenic Activity,” Bioorganic Chemistry 108, (2021): 104553.
  • B. M. Trost, “Atom Economy-A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way,” Angewandte Chemie International Edition in English 34, no. 3 (1995): 259–81.
  • P. A. Tempest, “Recent Advances in Heterocycle Generation Using the Efficient Ugi Multiple-Component Condensation Reaction,” Current Opinion in Drug Discovery & Development 8, (2005): 776–88.
  • H. Fujioka, K. Murai, O. Kubo, Y. Ohba, and Y. Kita, “New Three-Component Reaction: Novel Formation of a Seven-Membered Ring by the Unexpected Reaction at the gamma-position of the beta-keto ester ,” Organic Letters 9, no. 9 (2007): 1687–90.
  • N. M. Evdokimov, A. S. Kireev, A. A. Yakovenko, M. Y. Antipin, I. V. Magedov, and A. Kornienko, “One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols,” The Journal of Organic Chemistry 72, no. 9 (2007): 3443–53.
  • X. S. Wang, Q. Li, J. R. Wu, Y. L. Li, C. S. Yao, and S. J. Tu, “An Efficient and Highly Selective Method for the Synthesis of 3-Arylbenzoquinoline Derivatives Catalyzed by Iodine via Three-Component Reactions,” Synthesis 2008, no. 12 (2008): 1902–10.
  • P. A. Wender, S. T. Handy, and D. L. Wright, “Towards the Ideal Synthesis,” Chemistry and Industry 19, (1997): 765–9.
  • David J. Connolly, Declan Cusack, Timothy P. O'Sullivan, and Patrick J. Guiry, “Synthesis of Quinazolinones and Quinazolines,” Tetrahedron 61, no. 43 (2005): 10153–202.
  • M. G. A. Shvekhgeimer, “Synthesis of Heterocyclic Compounds Based on Isatoic Anhydrides (2H-3,1-Benzoxazine-2,4-Diones) (Review),” Chemistry of Heterocyclic Compounds 37, no. 4 (2001): 385–443.
  • M. Adib, E. Sheikhi, and H. R. Bijanzadeh, “One-Pot Three-Component Synthesis of 4 (3H)-Quinazolinones from Benzyl Halides, Isatoic Anhydride, and Primary Amines,” Synlett 2012, no. 01 (2012): 85–8.
  • R. Ramesh, G. Sankar, J. G. Malecki, and A. Lalitha, “Carbon–SO3H Derived from Glycerol: A Green Recyclable Catalyst for Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones,” Journal of the Iranian Chemical Society 15, no. 1 (2018): 1–9.
  • R. Ramesh, P. Kalisamy, J. G. Malecki, and A. Lalitha, “Metal-Free Mild Synthesis of Novel 1′ H-Spiro [Cycloalkyl-1, 2′-Quinazolin]-4′(3′ H)-Ones by an Organocatalytic Cascade Reaction,” Synlett 29, no. 02 (2018): 203–8.
  • K. Revathy, and A. Lalitha, “p-TSA-Catalyzed Synthesis of Spiroquinazolinones,” Journal of the Iranian Chemical Society 12, no. 11 (2015): 2045–9.

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