Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 54, 2024 - Issue 9
103
Views
0
CrossRef citations to date
0
Altmetric
Articles

KHSO4 promoted practical synthesis of quinazolin-4(3H)-ones and benzothiadiazine 1,1-dioxides

, , , , , , & show all
Pages 758-768 | Received 11 Feb 2024, Published online: 04 Apr 2024

References

  • Sonawane, V.; Mohd Siddique, M. U.; Jadav, S. S.; Sinha, B. N.; Jayaprakash, V.; Chaudhuri, B. Cink4T, a Quinazolinone-Based Dual Inhibitor of Cdk4 and Tubulin Polymerization, Identified via Ligand-Based Virtual Screening, for Efficient Anticancer Therapy. Eur. J. Med. Chem. 2019, 165, 115–132. DOI: 10.1016/j.ejmech.2019.01.011.
  • Hrast, M.; Rožman, K.; Jukič, M.; Patin, D.; Gobec, S.; Sova, M. Synthesis and Structure–Activity Relationship Study of Novel Quinazolinonebased Inhibitors of MurA. Bioorg. Med. Chem. Lett. 2017, 27, 3529–3533. DOI: 10.1016/j.bmcl.2017.05.064.
  • Yang, G.-Z.; Zhang, J.; Peng, J.-W.; Zhang, Z.-J.; Zhao, W.-B.; Wang, R.-X.; Ma, K.-Y.; Li, J.-C.; Liu, Y.-Q.; Zhao, Z.-M.; Shang, X.-F. Discovery of Luotonin a Analogues as Potent Fungicides and Insecticides: Design, Synthesis and Biological Evaluation Inspired by Natural Alkaloid. Eur. J. Med. Chem. 2020, 194, 112253. ;DOI: 10.1016/j.ejmech.2020.112253.
  • Nara, H.; Kaieda, A.; Sato, K.; Naito, T.; Mototani, H.; Oki, H.; Yamamoto, Y.; Kuno, H.; Santou, T.; Kanzaki, N.; et al. Discovery of Novel, Highly Potent, and Selective Matrix Metalloproteinase (MMP)-13 Inhibitors with a 1,2,4-Triazol-3-yl Moiety as a Zinc Binding Group Using a Structure-Based Design Approach. J. Med. Chem. 2017, 60, 608–626. DOI: 10.1021/acs.jmedchem.6b01007.
  • Kerdphon, S.; Khamto, N.; Buddhachat, K.; Ngoenkam, J.; Paensuwan, P.; Pongcharoen, S.; Singh, T.; Meepowpan, P.; Jongcharoenkamol, J. Structure-Activity Relationship and Molecular Docking of Quinazolinones Inhibiting Expression of COX-2, IL-1β, iNOS, and TNF-α through NF-κB Pathways. ACS Med. Chem. Lett. 2023, 14, 1167–1173. DOI: 10.1021/acsmedchemlett.3c00098.
  • Ellis, D. A.; Blazel, J. K.; Webber, S. E.; Tran, C. V.; Dragovich, P. S.; Sun, Z.; Ruebsam, F.; McGuire, H. M.; Xiang, A. X.; Zhao, J.; et al. 4-(1,1-Dioxo-1,4-Dihydro-1lambda6-Benzo[1,4]Thiazin-3-yl)-5-Hydroxy-2H-Pyridazin-3-Ones as Potent Inhibitors of HCV NS5B Polymerase. Bioorg. Med. Chem. Lett. 2008, 18, 4628–4632. DOI: 10.1016/j.bmcl.2008.07.014.
  • Pieterse, L.; van der Walt, M. M.; Terre’Blanche, G. C2-Substituted Quinazolinone Derivatives Exhibit A1 and/or A2A Adenosine Receptor Affinities in the Low Micromolar Range. Bioorg. Med. Chem. Lett. 2020, 30, 127274. DOI: 10.1016/j.bmcl.2020.127274.
  • Lv, L.; Maimaitiming, M.; Huang, Y.; Yang, J. C.; Chen, S. X.; Sun, Y. F.; Zhang, X. T.; Li, X.; Xue, C. H.; Wang, P. Y.; et al. Discovery of Quinazolin-4(3H)-One Derivatives as Novel AChE Inhibitors with anti-Inflammatory Activities. Eur. J. Med. Chem. 2023, 254, 115346. DOI: 10.1016/j.ejmech.2023.115346.
  • Li, F.; Lu, L.; Liu, P. C. Acceptorless Dehydrogenative Coupling of o-Aminobenzamides with the Activation of Methanol as a C1 Source for the Construction of Quinazolinones. Org. Lett. 2016, 18, 2580–2583. DOI: 10.1021/acs.orglett.6b00925.
  • Wang, G. W.; Miao, C. B.; Kang, H. Benign and Efficient Synthesis of 2-Substituted 4(3 H)-Quinazolinones Mediated by Iron(III) Chloride Hexahydrate in Refluxing Water. Bull. Chem. Soc. Jpn. 2006, 79, 1426–1430. DOI: 10.1246/bcsj.79.1426.
  • Yoshimura, T.; Jun, D. Y.; Kimura, Y.; Yamada, H.; Toshimitsu, A.; Kondo, T. Simple, Selective, and Practical Synthesis of 2-Substituted 4(3H)-Quinazolinones by Yb(OTf)3-Catalyzed Condensation of 2-Aminobenzamide with Carboxamides. Heterocycles 2015, 90, 857–865. DOI: 10.3987/COM-14-S(K)79.
  • Kerdphon, S.; Sanghong, P.; Chatwichien, J.; Choommongkol, V.; Rithchumpon, P.; Singh, T.; Meepowpan, P. Commercial Copper-Catalyzed Aerobic Oxidative Synthesis of Quinazolinones from 2-Aminobenzamide and Methanol. Eur J. Org Chem 2020, 2020, 2730–2734. DOI: 10.1002/ejoc.202000257.
  • Patil, B. N.; Lade, J. J.; Karpe, A. S.; Pownthurai, B.; Vadagaonkar, K. S.; Mohanasrinivasan, V.; Chaskar, A. C. Transition Metal-Catalyzed C H Functionalization of Arylacetic Acids for the Synthesis of Benzothiadiazine 1,1-Dioxides. Tetrahedron. Lett. 2019, 60, 891–894. DOI: 10.1016/j.tetlet.2019.02.031.
  • Du, P.; Zhou, H. F.; Sui, Y. B.; Liu, Q. X.; Zou, K. Asymmetric Synthesis of 3,4-Dihydro-2H-1,2,4-Benzothiadiazine-1,1- Dioxides Catalyzed by Scandium(III)-inda-Pybox. Tetrahedron. Lett. 2012, 72, 1573–1578. DOI101016/j.tet.2016.02.009. DOI: 10.1016/j.tet.2016.02.009.
  • Mishra, K.; Khanal, H. D.; Lee, Y. R. Facile N-Formylation of Amines on Magnetic Fe 3 O 4 −CuO Nanocomposites. Eur J. Org Chem 2021, 2021, 4477–4484. DOI: 10.1002/ejoc.202100872.
  • Guo, L. X.; Chen, Z. H.; Zhu, H. M.; Li, M. H.; Gu, Y. L. Acid-Catalyzed Chemodivergent Reactions of 2,2-Dimethoxyacetaldehyde and Anilines. Chin. Chem. Lett. 2021, 32, 1419–1422. DOI: 10.1016/j.cclet.2020.10.033.
  • Aridoss, G.; Laali, K. K. Building Heterocyclic Systems with RC(or) 2+ Carbocations in Recyclable Brønsted Acidic Ionic Liquids: Facile Synthesis of 1-Substituted 1 H -1,2,3,4-Tetrazoles, Benzazoles and Other Ring Systems with CH(OEt) 3 and EtC(OEt) 3 in [EtNH 3 ][NO 3 ] and [PMIM(so 3 H)][OTf]. Eur J. Org. Chem. 2011, 2011, 2827–2835. DOI: 10.1002/ejoc.201100128.
  • Gao, X.; Yu, B.; Mei, Q. Q.; Yang, Z. Z.; Zhao, Y. F.; Zhang, H.; Hao, L. D.; Liu, Z. M. Atmospheric CO 2 Promoted Synthesis of N-Containing Heterocycles over B(C 6 F 5) 3 Catalyst. New J. Chem. 2016, 40, 8282–8287. DOI: 10.1039/C6NJ01721E.
  • Bingi, C.; Kola, K. Y.; Kale, A.; Nanubolu, J. B.; Atmakur, K. A Simple One Pot Synthesis of Novel Tricyclic Quinazolinones. Tetrahedron. Lett. 2017, 58, 1071–1074. DOI: 10.1016/j.tetlet.2017.01.106.
  • Bie, Z. X.; Li, G. S.; Wang, L. Y.; Lv, Y.; Niu, J. Y.; Gao, S. A Facile Vanadium-Catalyzed Aerobic Oxidative Synthesis of Quinazolinones from 2-Aminobenzamides with Aldehydes or Alcohols. Tetrahedron. Lett. 2016, 57, 4935–4938. DOI: 10.1016/j.tetlet.2016.09.077.
  • Kim, N. Y.; Cheon, C. H. Synthesis of Quinazolinones from Anthranilamides and Aldehydes via Metal-Free Aerobic Oxidation in DMSO. Tetrahedron. Lett. 2014, 55, 2340–2344. DOI: 10.1016/j.tetlet.2014.02.065.
  • Abdullaha, M.; Mohammed, S.; Ali, M.; Kumar, A.; Vishwakarma, R. A.; Bharate, S. B. Discovery of Quinazolin-4(3 H)-Ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation. J. Org. Chem. 2019, 84, 5129–5140. DOI: 10.1021/acs.joc.9b00138.
  • Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F. Oxidative Synthesis of Quinazolinones and Benzothiadiazine 1,1-Dioxides from 2-Aminobenzamide and 2-Aminobenzenesulfonamide with Benzyl Alcohols and Aldehydes. RSC Adv. 2014, 4, 8–17. DOI: 10.1039/C3RA45765F.
  • Karpe, A. S.; Sathe, P. A.; Patil, P.; Patil, B. N.; Chaskar, A. C. Metal Free Oxidative C C Bond Cleavage: Facile and One-Pot Tandem Synthesis of Benzothiadiazine-1,1-Dioxides. Tetrahedron. Lett. 2019, 60, 1526–1529. DOI: 10.1016/j.tetlet.2019.05.002.
  • Wang, X. T.; Shang, S. Q.; Tian, Q. Q.; Wang, Y.; Wu, H. L.; Li, Z. Y.; Zhou, S. J.; Liu, H.; Dai, Z. S.; Luo, W.; et al. Imidazolium Chloride as an Additive for Synthesis of 4(3H)-Quinazolinones Using Anthranilamides and DMF Derivatives. Tetrahedron 2020, 76, 131480. DOI: 10.1016/j.tet.2020.131480.
  • Wang, R. Z.; Liu, S. Y.; Li, L. F.; Song, A.; Yu, S.; Zhuo, S.; Xing, S. P.; Mol, L. B. Metal-Free Catalyst for the Visible-Light-Induced Photocatalytic Synthesis of Quinazolinones. Catal 2021, 509, 111668. DOI: 10.1016/j.mcat.2021.111668.
  • Azizi, N.; Abbasi, F.; Abdoli-Senejani, M. Thiamine Immobilized on Silane-Functionalized Magnetic Nanoparticles for Catalytic Synthesis of 2,3-Dihydroquinazolin-4(1 H)-Ones in Water. Mater. Chem. Phys. 2017, 196, 118–125. DOI: 10.1016/j.matchemphys.2017.04.041.
  • Azizi, N.; Shirdel, F. Cholinesulfuric Acid Ionic Liquid Catalyzed an Eco-Friendly Synthesis of 2,3-Dihydroquinazolin-4(1H)-One in Aqueous Media. Res. Chem. Intermed. 2017, 43, 3873–3882. DOI: 10.1007/s11164-016-2849-4.
  • Paparakis, A.; Hulla, M. Frustrated Lewis Pairs Catalyse the Solvent-Assisted Synthesis of Azoles from Ortho-Substituted Anilines, CO 2 and H 2. ChemCatChem 2023, 15, e202300510. DOI: 10.1002/cctc.202300510.
  • Phatake, V. V.; Bhanage, B. M. Cu@U-g-C3N4 Catalyzed Cyclization of o-Phenylenediamines for the Synthesis of Benzimidazoles by Using CO2 and Dimethylamine Borane as a Hydrogen Source. Cata.l Lett. 2019, 149, 347–359. DOI: 10.1007/s10562-018-2608-9.
  • Jacquet, O.; Das Neves Gomes, C.; Ephritikhine, M.; Cantat, T. Complete Catalytic Deoxygenation of CO 2 into Formamidine Derivatives. ChemCatChem 2013, 5, 117–120. DOI: 10.1002/cctc.201200732.
  • Mokhtary, M.; Mahooti, K. Recent advances in the synthesis of highly substituted piperidine analogs with biological activities. Adv. J. Chem. Sect. A. 2024, 7, 163–189. DOI: 10.48309/ajca.2024.422013.1436.
  • Hakimi, F.; Taghvaee, M.; Golrasan, E..Synthesis of benzoxazole derivatives using Fe3O4@SiO2-SO3H nanoparticles as a useful and reusable heterogeneous catalyst without using a solvent. Adv. J. Chem. Sect. A. 2023, 6, 188–197. DOI: 10.22034/AJCA.2023.393949.1364.
  • Tajudeen Bale, A.; Mojisola Fasina, T.; Olarewaju Shaibu, R. Synthesis and biological study of substituted 2’’-Hydoxy, 2”,4”-dichloro chalcones and their Co(II), Cu(II) and Ni(II) complexes for their antioxidant and antimicrobial potentials. Adv. J. Chem. Sect. A. 2022, 5, 94–103. DOI: 10.22034/AJCA.2022.321509.1293.
  • Gan, Z. J.; Tian, B. H.; Yuan, J. Y.; Ran, D. Z.; Zhang, L.; Dong, G.; Pan, T.; Zeng, Y. X.; Yu, Y. A KHSO4 Promoted Tandem Synthesis of 1,3,4-Thiadiazoles from Thiohydrazides and DMF Derivatives. Tetrahedron. Lett. 2020, 61, 152195. DOI: 10.1016/j.tetlet.2020.152195.
  • Long, B. Y.; Tian, B. H.; Tang, Q.; Hu, X. N.; Han, L.; Wang, Z. F.; Wang, C. Y.; Wu, Y.; Yu, Y.; Gan, Z. J. A KHSO4 Mediated Facile Synthesis of 2-Amino-1,3,4-Oxadiazole Derivatives. Tetrahedron 2021, 96, 132382. DOI: 10.1016/j.tet.2021.132382.
  • Jin, H.; Cai, Q.; Liu, P. W.; Chen, Y.; Wang, D. R.; Zhu, W. P.; Xu, Y. F.; Qian, X. H. Multistep Continuous Flow Synthesis of Erlotinib. Chin. Chem. Lett. 2024, 35, 108721. DOI: 10.1016/j.cclet.2023.108721.
  • Deng, P.; Sun, G.; Zhao, J.; Yao, K. T.; Yuan, M. M.; Peng, L. Z.; Mao, L. F. Synthesis and Antitumor Activity of Erlotinib Derivatives Linked with 1,2,3-Triazole. Front. Pharmacol. 2021, 12, 793905. DOI: 10.3389/fphar.2021.793905.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.