142
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

A Versatile New Approach to Bridgehead Nitrogen Bearing Benzimidazolo-Quinazoline Hybrids: Facile 1,4-Dipolar Cycloaddition of Benzyne and N-(1H-Benzo[d]Imidazol-2-yl)-1-Phenylmethanimines

, , & ORCID Icon
Pages 5582-5590 | Received 18 May 2022, Accepted 18 Jul 2022, Published online: 02 Aug 2022

References

  • S. Ramesh and R. Nagarajan, “Copper-Catalyzed Hydroarylation of Alkynes for the Synthesis of Fascaplysin, Rutacarpine and Granulatimide Analogues,” Synthesis 47, no. 22 (2015): 3573–82.
  • X. Pan and T. D. Bannister, “Sequential Sonagashira and Larock Indole Synthesis Reactions in a General Strategy to Prepare Biologically Active β-Carboline-Containing Alkaloids,” Organic Letters 16, no. 23 (2014): 6124–7.
  • P. S. Baran and E. J. Corey, “A Short Synthetic Route to (+)-Austamide, (+)-Deoxyisoaustamide, and (+)-Hydratoaustamide from a Common Precursor by a Novel Palladium-Mediated Indole Dihydroindoloazocine Cyclization,” Journal of the American Chemical Society 124, no. 27 (2002): 7904–5.
  • Q. Li, J. Jiang, A. Fan, Y. Cui, and Y. Jia, “Total Synthesis of Lamellarins D, H, and R and Ningalin B,” Organic Letters 13, no. 2 (2011): 312–5.
  • S. De, S. Ghosh, S. Bhunia, J. A. Sheikh, and A. Bisai, “Intramolecular Direct Dehydrohalide Coupling Promoted by KOtBu: Total Synthesis of Amaryllidaceae Alkaloids Anhydrolycorinone and Oxoassoanine,” Organic Letters 14, no. 17 (2012): 4466–9.
  • M. Matveenko, O. J. Kokas, M. G. Banwell, and A. C. Willis, “Chemoenzymatic Approaches to Lycorine-Type Amaryllidaceae Alkaloids: Total Syntheses of Ent-Lycoricidine, 3-Epi-Ent-Lycoricidine, and 4-Deoxy-3-Epi-Ent-Lycoricidine,” Organic Letters 9, no. 18 (2007): 3683–5.
  • S. Yu, Q.-Q. Huang, Y. Luo, and W. Lu, “Total Synthesis of Camptothecin and SN-38,” The Journal of Organic Chemistry 77, no. 1 (2012): 713–7.
  • A. A. Leslie Gunatilaka, “Chapter, 1 – Alkaloids from Sri Lankan Flora,” The Alkaloids: Chemistry and Biology, vol. 52 (Cambridge, USA: Academic Press, 1999), 1–101.
  • D. R. Mehta, J. S. Naravane, and R. M. Desai, “Vasicinone. A Bronchodilator Principle from Adhatoda Vasica Nees (N. O. Acanthaceae),” The Journal of Organic Chemistry 28, no. 2 (1963): 445–8.
  • P. Mucci-LoRusso, L. Polin, M. C. Bissery, F. Valeriote, J. Plowman, G. D. Luk, and T. H. Corbett, “Activity of Batracylin (NSC-320846) against Solid Tumors of Mice,” Investigational New Drugs 7, no. 4 (1989): 295–306.
  • S. Ahamad, S. Branch, S. Harrelson, M. K. Hussain, M. Saquib, and S. Khan, “Primed for Global Coronavirus Pandemic: Emerging Research and Clinical Outcome,” European Journal of Medicinal Chemistry 209 (2021): 112862.
  • D. Kim, L. Wang, M. Beconi, G. J. Eiermann, M. H. Fisher, H. He, G. J. Hickey, J. E. Kowalchick, B. Leiting, K. Lyons, et al, “(2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-Dihydro[1,2,4]Triazolo[4,3-a]Pyrazin-7(8H)-yl]-1-(2,4,5-Trifluorophenyl)Butan-2-Amine: A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2” Diabetes,” Journal of Medicinal Chemistry 48, no. 1 (2005): 141–51.
  • C. J. Menet, S. R. Fletcher, G. V. Lommen, R. Geney, J. Blanc, K. Smits, N. Jouannigot, P. Deprez, E. M. van der Aar, P. Clement-Lacroix, et al., “Triazolopyridines as Selective JAK1 Inhibitors: From Hit Identification to GLPG0634,” Journal of Medicinal Chemistry 57, no. 22 (2014): 9323–42.
  • P. Norman, ” “Selective JAK Inhibitors in Development for Rheumatoid Arthritis,” Expert Opinion on Investigational Drugs 23, no. 8 (2014): 1067–77.
  • B. A. Johns, T. Kawasuji, J. G. Weatherhead, T. Taishi, D. P. Temelkoff, H. Yoshida, T. Akiyama, Y. Taoda, H. Murai, R. Kiyama, et al, “Carbamoyl Pyridone HIV-1 Integrase Inhibitors 3. A Diastereomeric Approach to Chiral Nonracemic Tricyclic Ring Systems and the Discovery of Dolutegravir (S/GSK1349572) and (S/GSK1265744),” Journal of Medicinal Chemistry 56, no. 14 (2013): 5901–16.
  • D. L. Hughes, “Review of the Patent Literature: Synthesis and Final Forms of Antiviral Drugs Tecovirimat and Baloxavir Marboxil,” Organic Process Research & Development 23, no. 7 (2019): 1298–307.
  • F. Tufail, S. Singh, M. Saquib, J. Tiwari, J. Singh, J. Singh. “Catalystfree, glycerol assisted facile approach to imidazole fused nitrogen-bridgehead heterocycles,” ChemistrySelect 2 (2017): 6082– 89.
  • D. Chernyak, and V. Gevorgyan, “Two-Component Approach toward a Fully Substituted N-Fused Pyrrole Ring,” Organic Letters 12, no. 23 (2010): 5558–60.
  • J. K. Laha and G. D. Cuny, “Synthesis of Fused Imidazoles, Pyrroles, and Indoles with a Defined Stereocenter α to Nitrogen Utilizing Mitsunobu Alkylation Followed by Palladium-Catalyzed Cyclization,” The Journal of Organic Chemistry 76, no. 20 (2011): 8477–82.
  • P. K. Gupta, M. A. Azzam, M. Saquib, and M. K. Hussain, “A Highly Efficient and Eco-Friendly Synthesis of Disubstituted Imidazoles in Ionic Liquid from Gem-Dibromo Vinylarenes and Amidines,” Polycyclic Aromatic Compounds (2022). doi: 10.1080/10406638.2022.2061532.
  • J. VelIk, V. Baliharova, J. F. Gremmels, S. Bull, J. Lamka, and L. Skalova, “Benzimidazole Drugs and Modulation of Biotransformation Enzymes,” Research in Veterinary Science 76, no. 2 (2004): 95–108.
  • Anelia Ts Mavrova, Kamelya K. Anichina, Dimitar I. Vuchev, Jordan A. Tsenov, Magdalena S. Kondeva, and Mitka K. Micheva, “Synthesis and Antitrichinellosis Activity of Some 2-Substituted-[1,3]Thiazolo[3,2-a]Benzimidazol-3(2H)-Ones,” Bioorganic & Medicinal Chemistry 13, no. 19 (2005): 5550–9.
  • Hakan Göker, Canan Kuş, David W. Boykin, Sulhiye Yildiz, and Nurten Altanlar, “Synthesis of Some New 2-Substituted-Phenyl-1H-Benzimidazole-5-Carbonitriles and Their Potent Activity against Candida Species,” Bioorganic & Medicinal Chemistry 10, no. 8 (2002): 2589–96.
  • M. M. Ramla, M. A. Omar, A. M. M. El-Khamry, and H. I. El-Diwani, “Synthesis and Antitumor Activity of 1-Substituted-2-Methyl-5-Nitrobenzimidazoles,” Bioorganic & Medicinal Chemistry 14, no. 21 (2006): 7324–32.
  • M. Boiani and M. Gonzalez, “Imidazole and Benzimidazole Derivatives as Chemotherapeutic Agents,” Mini Reviews in Medicinal Chemistry 5, no. 4 (2005): 409–24.
  • N. Malecki, P. Carato, G. Rigo, J. F. Goossens, R. Houssin, C. Bailly, and J. P. Henichart, “Synthesis of Condensed Quinolines and Quinazolines as DNA Ligands,” Bioorganic & Medicinal Chemistry 12, no. 3 (2004): 641–7.
  • A. Lewerenz, S. Hentschel, Z. Vissiennon, S. Michael, and K. Nieber, “A3 Receptors in Cortical Neurons: Pharmacological Aspects and Neuroprotection during Hypoxia,” Drug Development Research 58, no. 4 (2003): 420–7.
  • T. Herget, M. Freitag, M. Morbitzer, R. Kupfer, T. Stamminger, and M. Marschall, “Novel Chemical Class of pUL97 Protein Kinase-Specific Inhibitors with Strong Anticytomegaloviral Activity Antimicrob,” Antimicrobial Agents and Chemotherapy 48, no. 11 (2004): 4154–62.
  • K. Waisser, J. Gregor, H. Dostal, J. Kunes, L. Kubicova, V. Klimesova, and J. Kaustova, “Influence of the Replacement of the Oxo Function with the Thioxo Group on the Antimycobacterial Activity of 3-Aryl-6,8-Dichloro-2H-1,3-Benzoxazine-2,4(3H)-Diones and 3-Arylquinazoline-2,4(1H,3H)-Diones,” Il Farmaco 56, no. 10 (2001): 803–7.
  • H. Zhang, Y. Jin, H. Liu, Y. Jiang, and H. Fu, “Copper-Catalyzed Cascade Synthesis of 1H-Indolo[1,2-c]Quinazoline Derivatives,” European Journal of Organic Chemistry 2012, no. 34 (2012): 6798–803.
  • C. Li, W. T. Zhang, and X. S. Wang, “CuI-Catalyzed C–N Bond Formation and Cleavage for the Synthesis of Benzimidazo[1,2-a]Quinazoline Derivatives,” The Journal of Organic Chemistry 79, no. 12 (2014): 5847–51.
  • S. Guo, J. Wang, X. Fan, X. Zhang, and D. Guo, “Synthesis of Pyrazolo[1,5-c]Quinazoline Derivatives through Copper-Catalyzed Tandem Reaction of 5-(2-Bromoaryl)-1H-Pyrazoles with Carbonyl Compounds and Aqueous Ammonia,” The Journal of Organic Chemistry 78, no. 7 (2013): 3262–70.
  • M. Jiang, J. Li, F. Wang, Y. Zhao, F. Zhao, X. Dong, and W. Zhao, “A Facile Copper-Catalyzed One-Pot Domino Synthesis of 5,12-Dihydroindolo[2,1-b]Quinazolines,” Organic Letters 14, no. 6 (2012): 1420–3.
  • P. Sang, Y. Xie, J. Zou, and Y. Zhang, “Copper-Catalyzed Sequential Ullmann N-Arylation and Aerobic Oxidative C–H Amination: A Convenient Route to Indolo[1,2-c]Quinazoline Derivatives,” Organic Letters 14, no. 15 (2012): 3894–7.
  • B. S. Kuarm, Y. T. Reddy, J. V. Madhav, P. A. Crooks, and B. Rajitha, “3-[Benzimidazo- and 3-[Benzothiadiazoleimidazo-(1,2-c)Quinazolin-5-yl]-2H-Chromene-2-Ones as Potent Antimicrobial Agents,” Bioorganic & Medicinal Chemistry Letters 21, no. 1 (2011): 524–7.
  • P. Singla, V. Luxami, and K. Paul, “Quinazolinone-Benzimidazole Conjugates: Synthesis, Characterization, Dihydrofolate Reductase Inhibition, DNA and Protein Binding Properties,” Journal of Photochemistry and Photobiology. B, Biology 168 (2017): 156–64.
  • N. K. Nandwana, R. P. Singh, O. P. S. Patel, S. Dhiman, H. K. Saini, P. N. Jha, and A. Kumar, “Design and Synthesis of Imidazo/Benzimidazo[1,2-c]Quinazoline Derivatives and Evaluation of Their Antimicrobial Activity,” ACS Omega 3, no. 11 (2018): 16338–46.
  • Aiping Huang, Yimu Chen, Yige Zhou, Wei Guo, Xiaodong Wu, and Chen Ma, “An Efficient One-Pot Synthesis of Benzo[4,5]Imidazo[1,2-a]Quinoxalines via Copper-Catalyzed Process,” Organic Letters 15, no. 21 (2013): 5480–3.
  • S. Fang, X. Niu, B. Yang, Y. Li, X. Si, L. Feng, and C. Ma, “One-Pot Regioselective Synthesis of Benzo[4,5]Imidazo[1,2-a]Quinazoline Derivatives via Facile Transition Metal-Free Tandem Process,” ACS Combinatorial Science 16, no. 7 (2014): 328–32.
  • X. Ji, Y. Zhou, J. Wang, L. Zhao, H. Jiang, and H. Liu, “Au(I)/Ag(I)-Catalyzed Cascade Approach for the Synthesis of Benzo[4,5]Imidazo[1,2-c]Pyrrolo[1,2-a]Quinazolinones,” The Journal of Organic Chemistry 78, no. 9 (2013): 4312–8.
  • W. Chen, Y. Du, M. Wang, Y. Fang, W. Yu, and J. Chang, “Synthesis of Benzo[4,5]Imidazo[1,2-a]Quinoxalines by I2-Mediated sp3 C − H Amination,” Organic Chemistry Frontiers 7, no. 22 (2020): 3705–8.
  • Antonio Da Settimo, Giampaolo Primofiore, Federico Da Settimo, Gianluca Pardi, Francesca Simorini, and Anna Maria Marini, “An Approach to Novel Fused Triazole or Tetrazole Derivatives Starting from Benzimidazo[1,2-a]Quinazoline-5(7H)-One and 5,7-Dihydro-5-Oxopyrido[3′,2′:5,6]Pyrimido[1,2-a]Benzimidazoles,” Journal of Heterocyclic Chemistry 39, no. 5 (2002): 1007–11.
  • P. D. Q. Dao, S. L. Ho, and C. S. Cho, “Synthesis of N-Fused Benzimidazole-4,7-Diones via Sequential Copper-Catalyzed C − N Coupling/Cyclization and Oxidation,” ACS Omega 3, no. 5 (2018): 5643–53.
  • C. Shen, L. Wang, M. Wen, H. Shen, J. Jin, and P. Zhang, “Synthesis of Benzimidazo[1,2-c]Quinazolines via Metal-Free Intramolecular C − H Amination Reaction,” Industrial & Engineering Chemistry Research 55, no. 11 (2016): 3177–81.
  • N. K. Nandwana, K. Pericherla, P. Kaswan, and A. Kumar, “Synthesis of Novel Azole-Fused Quinazolines via One-Pot, Sequential Ullmann-Type Coupling and Intramolecular Dehydrogenative C–N Bonding,” Organic & Biomolecular Chemistry 13, no. 10 (2015): 2947–50.
  • D. Hong, Z. Chen, X. Lin, and Y. Wang, “Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates,” Organic Letters 12, no. 20 (2010): 4608–11.
  • D. McAusland, S. Seo, D. G. Pintori, J. Finlayson, and M. F. Greaney, “The Benzyne Fischer-Indole Reaction,” Organic Letters 13, no. 14 (2011): 3667–9.
  • Z. Qiu and Z. Xie, “Nickel-Catalyzed Three-Component [2 + 2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes,” Angewandte Chemie International Edition 48, no. 31 (2009): 5729–32.
  • M. Jeganmohan, S. Bhuvaneswari, and C. H. Cheng, “Angew. cooperative Copper- and Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Epoxides, and Terminal Alkynes,” Angewandte Chemie International Edition 48, no. 2 (2009): 391–4.
  • F. Sha and X. Huang, “Benzannulated Bicycles by Three-Component Aryne Reactions,” Angewandte Chemie International Edition 121, no. 19 (2009): 3510–3.
  • Alastair A. Cant, Guillaume H. V. Bertrand, Jaclyn L. Henderson, Lee Roberts, and Michael F. Greaney, “The Benzyne Aza-Claisen Reaction,” Angewandte Chemie International Edition 121, no. 28 (2009): 5301–4.
  • D. Gilmore, K. M. Allan, and B. M. Stoltz, “Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation,” Journal of the American Chemical Society 130, no. 5 (2008): 1558–9.
  • U. K. Tambar and B. M. Stoltz, “The Direct Acyl-Alkylation of Arynes,” Journal of the American Chemical Society 127, no. 15 (2005): 5340–1.
  • Z. Liu and R. C. Larock, “Intermolecular C − N Addition of Amides and S − N Addition of Sulfinamides to Arynes,” Journal of the American Chemical Society 127, no. 38 (2005): 13112–3.

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.