141
Views
1
CrossRef citations to date
0
Altmetric
Letters

Synthesis of Novel Dihydrothieno- and Thiopyrano Quinolines from 3-Formyl-2-Mercaptoquinoline Derivatives

, ORCID Icon, , ORCID Icon &
Pages 1406-1416 | Received 04 Jul 2018, Accepted 24 Nov 2018, Published online: 29 Jan 2019

References

  • W. Xue and D. Warshawsky, “Metabolic Activation of Polycyclic and Heterocyclic Aromatic Hydrocarbons and DNA Damage: A Review,” Toxicology and Applied Pharmacology 206 (2005): 73–93.
  • X. M. Peng, G. L. V. Damu, and H. Zhou, “Current Developments of Coumarin Compounds in Medicinal Chemistry,” Current Pharmaceutical Design 19 (2013): 3884–930.
  • H. Villar, M. Frings, and C. Bolm, “Ring Closing Enyne Metathesis: A Powerful Tool for the Synthesis of Heterocycles,” Chemical Society Reviews 36 (2007): 55–66.
  • A. Z. Halimehjani, I. N. Namboothiri, and S. E. Hooshmand, “Part II: Nitroalkenes in the Synthesis of Heterocyclic Compounds,” RSC Advances 4 (2014): 51794–829.
  • L. Q. Lu, J. R. Chen, and W. J. Xiao, “Development of Cascade Reactions for the Concise Construction of Diverse Heterocyclic Architectures,” Accounts of Chemical Research 45 (2012): 1278–93.
  • H. Liu, and X. Jiang, “Transfer of Sulfur: from Simple to Diverse,” Asian Journal of Chemistry 8 (2013): 2546–63; M. A. M. Massoud, W. A. Bayoumi, A. A. Farahat, M. A. El-Sayed, and B. Mansour, Arkivoc i (2018): 244–87.
  • Ibid.
  • A. Beauchard, A. Jaunet, L. Murillo, B. Baldeyrou, A. Lansiaux, J. R. Cherouvrier, L. Domon, L. Picot, C. Bailly, T. Besson, and V. Thiery, “Synthesis and Antitumoral Activity of Novel Thiazolobenzotriazole, Thiazoloindolo [3, 2-c] Quinoline and Quinolinoquinoline Derivatives,” European Journal of Medicinal Chemistry 44 (2009): 3858–65; A. Bolognese, G. Correale, M. Manfra, A. Esposito, E. Novellino, and A. Lavecchia, “Antitumor Agents 6. Synthesis, Structure-Activity Relationships, and Biological Evaluation of Spiro [Imidazolidine-4, 3′-Thieno [2, 3-g] Quinoline]-Tetraones and Spiro [Thieno [2,3-g] Quinoline-3,5′-[1,2,4] Triazinane]-Tetraones with Potent Antiproliferative Activity,” Journal of Medicinal Chemistry 51 (2008): 8148–57; J. A. Spicer, S. A. Gamage, G. J. Atwell, G. J. Finlay, B. C. Baguley, and W. A. Denny, “Structure- Activity Relationships for Acridine-Substituted Analogues of the Mixed Topoisomerase I/II Inhibitor N-[2-(Dimethylamino) ethyl] acridine-4-carboxamide,” Journal of Medicinal Chemistry 40 (1997): 1919–29.
  • M. N. Zemtsova, A. V. Zimichev, P. L. Trakhtenberg, R. S. Belen’kaya, and E. I. Boreko, “Synthesis and Antiviral Activity of 4-Quinolinecarboxylic acid Hydrazides,” Pharmaceutical Chemistry Journal 4 (2008): 571–3.
  • M. Kidwai, K. R. Bhushan, P. Sapra, R. K. Saxena, and R. Gupta, “Alumina-Supported Synthesis of Antibacterial Quinolines Using Microwaves,” Bioorganic & Medicinal Chemistry 8 (2000): 69–72.
  • H. Shiraki, M. P. Kozar, V. Mlelndez, T. H. Hudson, C. Ohrt, A. J. Magill, and Ai. J. Lin, “Antimalarial Activity of Novel 5-aryl-8-Aminoquinoline Derivatives,” Journal of Medicinal Chemistry 54 (2011): 131–42; K. Kaur, M. Jain, R. P. Reddy, and R. Jain. “Quinolines and Structurally Related Heterocycles as Antimalarials,” European Journal of Medicinal Chemistry 45 (2010): 3245–64.
  • C. M. Lu, Y. L. Chen, H. L. Chen, C. A. Chen, P. J. Lu, C. N. Yang, and C. C. Tzeng, “Synthesis and Antiproliferative Evaluation of Certain Indolo [3, 2-c] Quinoline Derivatives,” Bioorganic & Medicinal Chemistry 18 (2010): 1948–57; C. H. Tseng, Y. L. Chen, K. Y. Chung, C. M. Cheng, C. H. Wang, and C. C. Tzeng, “Synthesis and antiproliferative Evaluation of 6-Arylindeno [1, 2-c] Quinoline Derivatives,” Bioorganic & Medicinal Chemistry 17 (2009): 7465–76.
  • D. Dub, M. Blouin, C. Brideau, C. Chan, C. Desmarais, D. Ethier, J. P. Falgueyret, R. W. Friesen, M. Girard, Y. Girard, et al., “Quinolines as Potent 5-Lipoxygenase Inhibitors: Synthesis and Biological Profile of L-746,530,” Bioorganic & Medicinal Chemistry Letter 8 (1998): 1255–60.
  • R. D. Dillard, D. E. Pavey, and D. N. Benslay, “Synthesis and Antiinflammatory Activity of Some 2, 2-Dimethyl-1, 2-Dihydroquinolines,” Journal of Medicinal Chemistry 16 (1973): 251–3; B. J. Mulchin, C. G. Newton, J. W. Baty, C. H. Grasso, W. J. Martin, M. C. Walton, E. M. Dangerfield, C. H. Plunkett, M. V. Berridge, J. L. Harper, et al, “The Anti-Cancer, Anti-Inflammatory and Tuberculostatic Activities of a Series of 6, 7-Substituted-5, 8-Quinolinequinones,” Bioorganic & Medicinal Chemistry 18 (2010): 3238–51.
  • F. Rechfeld, P. Gruber, J. Kirchmair, M. Boehler, N. Hauser, G. Hechenberger, D. Garczarczyk, G. B. Lapa, M. N. Preobrazhenskaya, P. Goekjian, T. Langer, and J. Hofmann, “Thienoquinolines as Novel Disruptors of the PKCε/RACK2 Protein-Protein Interaction,” Journal of Medicinal Chemistry 57 (2014): 3235–46.
  • R. P. Srivastava and A. P. Bhaduri, “Synthetic Applications of 2‐Chloro‐3‐Formylquinoline,” Journal of Heterocyclic Chemistry 24 (1987): 219–22.
  • A. Abdel-Rahma, E. A. Bakhite, M. I. Abdel-Moneam, and Th. A. Mohamed, “Synthesis and Antibacterial Activities of Some New Thieno-[2, 3-b] Quinolines,” Phosphorus, Sulfur, and Silicon and the Related Elements 75 (1993): 219.
  • A. Hafez Abdel, A. M. Kamal El Dean, A. A. Hassan, and H. S. El-Kashef, “Synthesis and Biological Activity of Some New Pyrimidothienoquinolines,” Bulletin of Faculty of Science 23 (1994): 93–107.
  • A. A. Geies, E. A. Bakhite, and H. S. El-Kashef, “Synthesis and Antimicrobial Activities of Some New Pyrrolylthieno [2, 3-b]-Quinoline Derivatives,” Pharmazie 53 (1998): 686–90.
  • G. Wagner, H. Vieweg, and S. Leistner, “Synthesis of 11-Aryl-7, 8, 9, 10-Tetrahydro-1, 2, 3-Triazino-(4', 5': 4, 5)-Thienol-(2, 3-b)-Quinolines with Aantianaphylactic Action,” Pharmazie 48 (1993): 576–8.
  • E. A. Harrison, Jr.K. C. Rice, and M. E. Rogers, “Synthesis, Phosphodiesterase Inhibition and Antiinflammatory Activity of 2‐aryl‐3‐Hydroxythieno [2, 3‐b] Quinoline 1, 1‐Dioxides. Application of Sodium Chlorite as a Novel Reagent for the (Stepwise) Oxidation of Sulfides to Sulfones,” Journal of Heterocyclic Chemistry 14 (1977): 909–15.
  • P. Shanmugam, K. Kanakarajan, N. Soundararajan, and A. Gnanasekaran, “Thienoquinolines Part 1. Synthesis of Thieno [2, 3-b]-Quinolines,” Synthesis 4 (1976): 253–5.
  • B. P. Nandeshwarappa, D. B.Aruna Kumar, H. S. Bhojya Naik, and K. M. Mahadevan, “A Fast and Large-Scale Synthesis of 3-Formyl-2-Mercaptoquinolines,” Phosphorus, Sulfur, and Silicon, and the Related Elements 181 (2006): 1997–2003.
  • N. J. Parmar, H. A. Barad, B. M. Labana, R. Kant, and Vivek K. Gupta, “A Glycerol Mediated Domino Reaction: An Efficient, Green Synthesis of Polyheterocycles Incorporating A New Thiochromeno [2, 3-b] Quinoline Unit,” RSC Advances 3 (2013): 20719–25.
  • J. Gowda, A. Khader, B. Kalluraya, and S. Hidayathulla, “Synthesis, Characterization and Antibacterial Activity of Benzimidazole Derivatives Carrying Quinoline Moiety,” Indian Journal of Chemistry B 50 (2011): 1491–95.
  • B. M. Kiran, B. P. Nandeshwarappa, V. P. Vaidya, and K. M. Mahadevan, “Chemistry of Substituted Quinolines: Thieno [2, 3-b] and Thiopyrano [2, 3-b] Quinolines,” Phosphorus, Sulfur, and Silicon, and the Related Elements 182 (2007): 969–80.
  • F. Churruca, S. Hernandez, M. Perea, R. SanMartin, and E. Dominguez, “Direct Access to Pyrazolo (benzo) Thienoquinolines. Highly Effective Palladium Catalysts for the Intramolecular C-H Heteroarylation of Arenes,” Chemical Communications. 49 (2013): 1413–5.
  • E. Leung, L. I. Pilkington, M. van Rensburg, C. Y. Jeon, M. Song, H. J. Arabshahi, G. H. De Zoysa, V. Sarojini, W. A. Denny, J. Reynisson, et al., “Synthesis and Cytotoxicity of Thieno[2,3-b]Quinoline-2-Carboxamide and Cycloalkyl[b]thieno[3,2-e]pyridine-2-carboxamide Derivatives,” Bioorganic & Medicinal Chemistry 24 (2016): 1142–54.
  • A. P. Marjani, J. Khalafy, and A. Rostampoor, “The Synthesis of New Benzo [h] Thieno [2, 3‐b] Quinoline‐9‐yl (aryl) Methanone Derivatives,” Journal of Heterocyclic Chemistry 54 (2016): 648–52; A. Alizadeh, and A. Roosta, “Synthesis of a New Series of Aryl (Thieno [2, 3-b] Quinolin-2-yl) Methanone and 2-(2-Aroyl-2, 3-dihydrothieno [2, 3-b] Quinolin-3-yl)-1-arylethanone Derivatives via Sequential Multi-component Reaction,” Chemical Papers 72 (2018):1–12.
  • P. S. Wei, M. X. Wang, D. C. Xu, and J. W. Xie, “Synthesis of 2,3-Dihydrothieno(2,3-b)quinolines and Thieno(2,3-b)- Quinolines via an Unexpected Domino Aza-MBH/Alkylation/Aldol Reaction,” Journal of Organic Chemistry 81 (2016): 1216–22.
  • P. Salehi, M. Shiri. “Palladium-Catalyzed Highly Regioselective Synthesis of 3-(Hetero)arylpropynamides from gem-Dibromoalkenes and Isocyanides,” Advanced Synthesis & Catalysis DOI: 10.1002/adsc.201800963.
  • M. Shiri, M. A. Zolfigol, H. G. Kruger, and Z. Tanbakouchian, Advances in Heterocyclic Chemistry, edited by A. R. Katritzky (Oxford: Academic, 2011), vol. 185, 139.
  • Z. Faghihi, H. A. Oskooie, M. M. Heravi, M. Tajbakhsh, and M. Shiri, “A Novel Analogue of Asinger Reaction for the Synthesis of Thiazinoquinoline Derivatives,” Monatshefte für Chemie 148 (2017): 315–20.
  • M. Shiri, M. Ranjbar, Z. Yasaei, F. Zamanian, and B. Notash, “Palladium-Catalyzed Tandem Reaction of 2-Chloroquinoline-3-Carbaldehydes and Isocyanides,” Organic and Biomolecular Chemistry 15 (2017): 10073–81.
  • M. Shiri, R. Pourabed, V. Zadsirjan, and E. Sodagar, “Highly Selective Organocatalytic Three-Component Reaction of 2-Chloroquinoline-3-Carbaldehydes, 6-Aminouracils, and Cyclic Methylene Active Compounds,” Tetrahedron Letters 57 (2016): 5435–8.
  • M. Shiri, M. A. Zolfigol, M. Pirveysian, R. Ayazi-Nasrabadi, H. G. Kruger, T.Naicker, and I. Mohammad poor Baltork, “A New and Facile Access to the 2-(Indol-3-yl)-3-nitriloquinolines Based on Friedländer Annulations,” Tetrahedron 68 (2012): 6059.
  • M. Shiri, M. Fathollahi-Lahroud, and Z. Yasaei, “A Novel Strategy for the Synthesis of 6H-Chromeno [4, 3-b] Quinoline by Intramolecular Heck Cyclization,” Tetrahedron 73 (2017): 2501.
  • M. Shiri, M. Heydari, and V. Zadsirjan, “Efficient Synthesis of Novel Functionalized Pyrazolo-pyranoquinoline and Tetrahydrodibenzo-[1, 8] Naphthyridinone Derivatives,” Tetrahedron 73 (2017): 2116.
  • M. Shiri, Z. Faghihi, H. A. Oskouei, M. M. Heravi, S. Fazelzadeh, and B. Notash, “The Synthesis of Iminothiophenone-Fused Quinolines and Evaluation of Their Serendipitous Reactions,” RSC Advances 6 (2016): 92235.
  • M. Raghavendra, H. S. Bhojya Naik, T. R. Ravikumar Naik, and B. S. Sherigara, “A Facile One Pot Synthesis of Some New 2-Phenyl-2H-[1,3]thiazino [6, 5-b]quinolines under Microwave Irradiation in Solvent Free Conditions,” Journal of Sulfur Chemistry 6 (2007): 165–9; W. S., Hamama, M. E. Ibrahim, A. A. Gooda, and H. H. Zoorob, “Recent Advances in the Chemistry of 2-Chloroquinoline-3-carbaldehyde and Related Analogs,” RSC Advances 8 (2018): 8484–515.

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.