Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 1
226
Views
6
CrossRef citations to date
0
Altmetric
Articles

An efficient Pd-catalyzed intramolecular cyclization reaction followed by formation of benzimidazole derivatives: Synthesis of novel quinolin-fused benzo[d] azeto[1,2-a]benzimidazole analogues

, &
Pages 81-93 | Received 27 May 2020, Published online: 11 Sep 2020

References

  • Ricci, A, Ed. Amino Group Chemistry: From Synthesis to the Life Sciences. John Wiley & Sons: Weinheim, 2008.
  • Park, Y.; Kim, Y.; Chang, S. Transition Metal-Catalyzed C–H Amination: Scope, Mechanism, and Applications. Chem. Rev. 2017, 117, 9247–9301. DOI: 10.1021/acs.chemrev.6b00644.
  • Johansson Seechurn, C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium‐Catalyzed Cross‐Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. Engl. 2012, 51, 5062–5085. DOI: 10.1002/anie.201107017.
  • Tasler, S.; Mies, J.; Lang, M. Applicability Aspects of Transition Metal‐Catalyzed Aromatic Amination Protocols in Medicinal Chemistry. Adv. Synth. Catal. 2007, 349, 2286–2300. DOI: 10.1002/adsc.200700133.
  • Roughley, S. D.; Jordan, A. M. The Medicinal Chemist’s Toolbox: An Analysis of Reactions Used in the Pursuit of Drug Candidates. J. Med. Chem. 2011, 54, 3451–3479. DOI: 10.1021/jm200187y.
  • Cooper, T. W.; Campbell, I. B.; Macdonald, S. J. Factors Determining the Selection of Organic Reactions by Medicinal Chemists and the Use of These Reactions in Arrays (Small Focused Libraries). Angew. Chem. Int. Ed. Engl. 2010, 49, 8082–8091. DOI: 10.1002/anie.201002238.
  • Demirayak, Ş.; Mohsen, U. A.; Karaburun, A. Ç. Synthesis and Anticancer and Anti-HIV Testing of Some Pyrazino [1, 2-a] Benzimidazole Derivatives. Eur. J. Med. Chem. 2002, 37, 255–260. DOI: 10.1016/S0223-5234(01)01313-7.
  • Enumula, S.; Pangal, A.; Gazge, M.; Shaikh, J. A.; Ahmed, K. Diverse Pharmacological Aspects of Benzimidazole Derivatives: A Review. Res. J. Chem. Sci. 2014, 4, 78–88.
  • Kidwai, M.; Jahan, A.; Bhatnagar, D. Polyethylene Glycol: A Recyclable Solvent System for the Synthesis of Benzimidazole Derivatives Using CAN as Catalyst. J. Chem. Sci. 2010, 122, 607–612. DOI: 10.1007/s12039-010-0095-7.
  • Ansari, K. F.; Lal, C. Synthesis and Biological Activity of Some Heterocyclic Compounds Containing Benzimidazole and Beta-Lactam Moiety. J. Chem. Sci. 2009, 121, 1017–1025. DOI: 10.1007/s12039-009-0114-8.
  • Khabnadideh, S.; Rezaei, Z.; Pakshir, K.; Zomorodian, K.; Ghafari, N. Synthesis and Antifungal Activity of Benzimidazole, Benzotriazole and Aminothiazole Derivatives. Res. Pharm. Sci. 2012, 7, 65–72.
  • Aanandhi, M. V.; Verma, A. K.; Sujatha, R.; Raj, R. K. Synthesis and Characterization of Novel Mannich Bases of Benzimidazole Derivatives for Antibacterial and Antifungal Activity. Int. J. Pharm. Pharm. Sci. 2013, 5, 295–297. ISSN-0975-1491.
  • Kathrotiya, H. G.; Patel, M. P. An Efficient Synthesis of 3′-Indolyl Substituted Pyrido [1, 2-a] Benzimidazoles as Potential Antimicrobial and Antioxidant Agents. J. Chem. Sci. 2013, 125, 993–1001. DOI: 10.1007/s12039-013-0468-9.
  • Nabeel, B. H.; Farah, S. T. Synthesis and Structural Studies on Some Transition Metal Complexes of Bis-(Benzimidazole-2-Thio) Ethane, Propane and Butane Ligands. Res. J. Chem. Sci. 2012, 2, 43–49.
  • Nandha, B.; Nargund, L. V. G.; Nargund, S. L.; Kuntal, H. Design and Synthesis of Imidazolylmethyl Substituted Fluorobenzimidazoles for Antitubercular and Antifungal Activity. J. Chem. Pharm. Res. 2014, 6, 530–539.
  • Desai, N. C.; Shihory, N. R.; Kotadiya, G. M.; Desai, P. Synthesis, Antibacterial and Antitubercular Activities of Benzimidazole Bearing Substituted 2-Pyridone Motifs. Eur. J. Med. Chem. 2014, 82, 480–489. DOI: 10.1016/j.ejmech.2014.06.004.
  • Kalalbandi, V. K. A.; Seetharamappa, J.; Katrahalli, U.; Bhat, K. G. Synthesis, Crystal Studies, Anti-Tuberculosis and Cytotoxic Studies of 1-[(2E)-3-Phenylprop-2-Enoyl]-1H-Benzimidazole Derivatives. Eur. J. Med. Chem. 2014, 79, 194–202. DOI: 10.1016/j.ejmech.2014.04.017.
  • Shingalapur, R. V.; Hosamani, K. M.; Keri, R. S.; Hugar, M. H. Derivatives of Benzimidazole Pharmacophore: Synthesis, Anticonvulsant, Antidiabetic and DNA Cleavage Studies. Eur. J. Med. Chem. 2010, 45, 1753–1759. DOI: 10.1016/j.ejmech.2010.01.007.
  • Siddiqui, N.; Alam, M. S.; Ali, R.; Yar, M. S.; Alam, O. Synthesis of New Benzimidazole and Phenylhydrazinecarbothiomide Hybrids and Their Anticonvulsant Activity. Med. Chem. Res. 2016, 25, 1390–1402. DOI: 10.1007/s00044-016-1570-6.
  • Sondhi, S. M.; Rajvanshi, S.; Johar, M.; Bharti, N.; Azam, A.; Singh, A. K. Anti-Inflammatory, Analgesic and Antiamoebic Activity Evaluation of Pyrimido [1, 6-a] Benzimidazole Derivatives Synthesized by the Reaction of Ketoisothiocyanates with Mono and Diamines. Eur. J. Med. Chem. 2002, 37, 835–843. DOI: 10.1016/S0223-5234(02)01403-4.
  • Sondhi, S. M.; Singh, N.; Kumar, A.; Lozach, O.; Meijer, L. Synthesis, Anti-Inflammatory, Analgesic and Kinase (CDK-1, CDK-5 and GSK-3) Inhibition Activity Evaluation of Benzimidazole/Benzoxazole Derivatives and Some Schiff’s Bases. Bioorg. Med. Chem. 2006, 14, 3758–3765. DOI: 10.1016/j.bmc.2006.01.054.
  • Lazer, E. S.; Matteo, M. R.; Possanza, G. J. Benzimidazole Derivatives with Atypical Antiinflammatory Activity. J. Med. Chem. 1987, 30, 726–729. DOI: 10.1021/jm00387a026.
  • Gaba, M.; Singh, S.; Mohan, C. Benzimidazole: An Emerging Scaffold for Analgesic and Anti-Inflammatory Agents. Eur. J. Med. Chem. 2014, 76, 494–505. DOI: 10.1016/j.ejmech.2014.01.030.
  • Faidallah, H. M.; Khan, K. A.; Asiri, A. M. Synthesis of Some New 2-Oxo-1, 4-Disubstituted-1, 2, 5, 6-Tetrahydro-Benzo [h] Quinoline-3-Carbonitriles and Their Biological Evaluation as Cytotoxic and Antiviral Agents. J. Chem. Sci. 2012, 124, 625–631. DOI: 10.1007/s12039-011-0184-2.
  • Gomha, S. M.; Dawood, K. M. Synthesis of novel indolizine, pyrrolo [1, 2-a] quinoline, and 4, 5-dihydrothiophene derivatives via nitrogen ylides and their antimicrobial evaluation. J. Chem. Res. 2014, 38(9), 515–519. DOI: 10.3184/174751914X14067338307126.
  • Subramaniapillai, S. G. Mannich Reaction: A Versatile and Convenient Approach to Bioactive Skeletons. J. Chem. Sci. 2013, 125, 467–482. DOI: 10.1007/s12039-013-0405-y.
  • Wang, Z.; Zhou, L. J.; Wang, Y. L.; Weng, Y. B.; He, J.; Nie, K. Synthesis and Anticoccidial Activities of Substituted Ethyl 4-Hydroxy-11-Oxo-11 H-Chromeno [2, 3-g] Quinoline-3-Carboxylates. J. Chem. Res. (S) 2011, 35, 373–376. DOI: 10.3184/174751911X13090888724310.
  • Brandi, A.; Cicchi, S.; Cordero, F. M. Novel Syntheses of Azetidines and Azetidinones. Chem. Rev. 2008, 108, 3988–4035. DOI: 10.1021/cr800325e.
  • Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Rational Development of Practical Catalysts for Aromatic Carbon-Nitrogen Bond Formation. Acc. Chem. Res. 1998, 31, 805–818. DOI: 10.1021/ar9600650.
  • Mudaliar, S. S.; Zala, S. N.; Chikhalia, K. H. Copper Catalysed Alkylation of Heteroaryl Chloride via Migratory Insertion of Carbenes. J. Organomet. Chem. 2017, 848, 142–148. DOI: 10.1016/j.jorganchem.2017.07.006.
  • Alsabeh, P. G.; Lundgren, R. J.; Longobardi, L. E.; Stradiotto, M. Palladium-Catalyzed Synthesis of Indoles via Ammonia Cross-Coupling-Alkyne Cyclization. Chem. Commun. (Camb.) 2011, 47, 6936–6938. DOI: 10.1039/c1cc11874a.
  • Boger, D. L. Heterocyclic and Acyclic Azadiene Diels‐Alder Reactions: Total Synthesis of Nothapodytine B. J. Het. Chem. 1998, 35, 1003–1011. DOI: 10.1002/jhet.5570350502.
  • Lindley, J. Tetrahedron Report Number 163: Copper Assisted Nucleophilic Substitution of Aryl Halogen. Tetrahedron 1984, 40, 1433–1456. DOI: https://doi.org/10.1016/S0040-4020. (01)91791-0. DOI: 10.1016/S0040-4020(01)91791-0.
  • Old, D. W.; Harris, M. C.; Buchwald, S. L. Efficient Palladium-Catalyzed N-Arylation of Indoles. Org. Lett. 2000, 2, 1403–1406. DOI: 10.1021/ol005728z.
  • Nayak, M.; Batra, S. Synthesis of Substituted Pyrazolo [4, 3-b] Pyridines via Copper-Mediated Intramolecular C–N Cross-Coupling of Primary Allylamines. RSC Adv. 2012, 2, 3367–3373. DOI: 10.1039/C2RA01170K..
  • Patel, A. B.; Kumari, P.; Chikhalia, K. H. One-Pot Synthesis of Novel Quinoline-Fused Azeto [1, 2-a] Benzimidazole Analogs via Intramolecular Pd-Catalyzed C–N Coupling. Catal. Lett. 2014, 144, 1332–1338. DOI: 10.1007/s10562-014-1266-9.
  • Phukan, K.; Ganguly, M.; Devi, N. Mild and Useful Method for N-Acylation of Amines.‎ Synth. Commun. 2009, 39, 2694–2701. DOI: 10.1080/00397910802663428.

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.