Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2016 (2016), Article ID 9315614, 9 pages
http://dx.doi.org/10.1155/2016/9315614
Research Article

(+)-CSA Catalyzed Multicomponent Synthesis of 1-[(1,3-Thiazol-2-ylamino)methyl]-2-naphthols and Their Ring-Closure Reaction under Ultrasonic Irradiation

1Department of Chemistry, Faculty of Art and Sciences, Kirklareli University, Kayali Campus, 39100 Kırklareli, Turkey
2Department of Chemistry, Faculty of Art and Sciences, Yildiz Technical University, Davutpaşa Campus, 34210 Istanbul, Turkey

Received 12 February 2016; Accepted 29 March 2016

Academic Editor: Rajeev Sakhuja

Copyright © 2016 Emel Pelit and Zuhal Turgut. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. Dömling, “Recent developments in isocyanide based multicomponent reactions in applied chemistry,” Chemical Reviews, vol. 106, no. 1, pp. 17–89, 2006. View at Publisher · View at Google Scholar · View at Scopus
  2. J. Zhu, “Recent developments in the isonitrile-based multicomponent synthesis of heterocycles,” European Journal of Organic Chemistry, no. 7, pp. 1133–1144, 2003. View at Google Scholar · View at Scopus
  3. J. Zhu and H. Bienayme, Eds., Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2005.
  4. J. D. Sunderhaus and S. F. Martin, “Applications of multicomponent reactions to the synthesis of diverse heterocyclic scaffolds,” Chemistry—A European Journal, vol. 15, no. 6, pp. 1300–1308, 2009. View at Publisher · View at Google Scholar · View at Scopus
  5. A. Dömling and I. Ugi, “Multicomponent reactions with isocyanides,” Angewandte Chemie—International Edition, vol. 39, no. 18, pp. 3169–3210, 2000. View at Google Scholar · View at Scopus
  6. J. Zhu, Q. Wang, and M. X. Wang, Eds., Multicomponent Reactions in Organic Synthesis, Wiley-VCH, Weinheim, Germany, 2015.
  7. L. Pu and H.-B. Yu, “Catalytic asymmetric organozinc additions to carbonyl compounds,” Chemical Reviews, vol. 101, no. 3, pp. 757–824, 2001. View at Publisher · View at Google Scholar · View at Scopus
  8. R. Müller, H. Goesmann, and H. Waldmann, “N,N-phthaloylamino acids as chiral auxiliaries in asymmetric Mannich-type reactions,” Angewandte Chemie—International Edition, vol. 38, no. 1-2, pp. 184–187, 1999. View at Publisher · View at Google Scholar · View at Scopus
  9. M. Arend, B. Westermann, and N. Risch, “Modern variants of the Mannich reaction,” Angewandte Chemie—International Edition, vol. 37, no. 8, pp. 1044–1070, 1998. View at Google Scholar · View at Scopus
  10. S. G. Subramaniapillai, “Mannich reaction: a versatile and convenient approach to bioactive skeletons,” Journal of Chemical Sciences, vol. 125, no. 3, pp. 467–482, 2013. View at Publisher · View at Google Scholar · View at Scopus
  11. G. Roman, “Mannich bases in medicinal chemistry and drug design,” European Journal of Medicinal Chemistry, vol. 89, pp. 743–816, 2015. View at Publisher · View at Google Scholar · View at Scopus
  12. C. Chen, X. Zhu, Y. Wu et al., “5-Sulfosalicylic acid catalyzed direct Mannich reaction in pure water,” Journal of Molecular Catalysis A: Chemical, vol. 395, no. 1, pp. 124–127, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. Z. Guan, J. Song, Y. Xue, D.-C. Yang, and Y.-H. He, “Enzyme-catalyzed asymmetric Mannich reaction using acylase from Aspergillus melleus,” Journal of Molecular Catalysis B: Enzymatic, vol. 111, pp. 16–20, 2015. View at Publisher · View at Google Scholar · View at Scopus
  14. W.-J. Hao, B. Jiang, S.-J. Tu et al., “A new mild base-catalyzed Mannich reaction of hetero-arylamines in water: highly efficient stereoselective synthesis of β-aminoketones under microwave heating,” Organic & Biomolecular Chemistry, vol. 7, no. 7, pp. 1410–1414, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. U. C. Rajesh, R. Kholiya, V. Satya Pavan, and D. S. Rawat, “Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction,” Tetrahedron Letters, vol. 55, no. 18, pp. 2977–2981, 2014. View at Publisher · View at Google Scholar · View at Scopus
  16. V. Kavala, C. Lin, C.-W. Kuo, H. Fang, and C.-F. Yao, “Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction,” Tetrahedron, vol. 68, no. 4, pp. 1321–1329, 2012. View at Publisher · View at Google Scholar · View at Scopus
  17. C. Cimarelli, G. Palmieri, and E. Volpini, “A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde,” Tetrahedron: Asymmetry, vol. 13, no. 22, pp. 2417–2426, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. C. Cimarelli and G. Palmieri, “Synthesis of enantiopure 2-(Aminoalkyl)phenol derivatives and their application as catalysts in stereoselective reactions,” Chirality, vol. 21, no. 1, pp. 218–232, 2009. View at Publisher · View at Google Scholar · View at Scopus
  19. I. Szatmári and F. Fülöp, “Syntheses, transformations and applications of aminonaphthol derivatives prepared via modified Mannich reactions,” Tetrahedron, vol. 69, no. 4, pp. 1255–1278, 2013. View at Publisher · View at Google Scholar · View at Scopus
  20. E. Pelit and Z. Turgut, “Synthesis of enantiopure aminonaphthol derivatives under conventional/ultrasonic technique and their ring-closure reaction,” Arabian Journal of Chemistry, 2014. View at Publisher · View at Google Scholar · View at Scopus
  21. A. Shaabani, A. Rahmati, and E. Farhangi, “Water promoted one-pot synthesis of 2′-aminobenzothiazolomethyl naphthols and 5-(2′-aminobenzothiazolomethyl)-6-hydroxyquinolines,” Tetrahedron Letters, vol. 48, no. 41, pp. 7291–7294, 2007. View at Publisher · View at Google Scholar
  22. A. Hosseinian and H. R. Shaterian, “NaHSO4.H2O catalyzed multicomponent synthesis of 1-(Benzothiazolylamino) methyl-2-naphthols under solvent-free conditions,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 187, no. 9, pp. 1056–1063, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. Z. Li and X. Mao, “One-pot three-component solvent-free synthesis of 1-[(1,3-thiazol-2-ylamino)methyl]-2-naphthols,” Heterocyclic Communications, vol. 17, no. 5-6, pp. 219–222, 2011. View at Publisher · View at Google Scholar · View at Scopus
  24. K. N. Venugopala, M. Krishnappa, S. K. Nayak et al., “Synthesis and antimosquito properties of 2,6-substituted benzo[d]thiazole and 2,4-substituted benzo[d]thiazole analogues against Anopheles arabiensis,” European Journal of Medicinal Chemistry, vol. 65, no. 1, pp. 295–303, 2013. View at Publisher · View at Google Scholar · View at Scopus
  25. S. Javanshir, A. Ohanian, M. M. Heravi, M. R. Naimi-Jamal, and F. F. Bamoharram, “Ultrasound-promoted, rapid, green, one-pot synthesis of 2′-aminobenzothiazolomethylnaphthols via a multi-component reaction, catalyzed by heteropolyacid in aqueous media,” Journal of Saudi Chemical Society, vol. 18, no. 5, pp. 502–506, 2014. View at Publisher · View at Google Scholar · View at Scopus
  26. G. Chaubet, L. T. Maillard, J. Martinez, and N. Masurier, “A tandem aza-FriedeleCrafts reaction/Hantzsch cyclization: a simple procedure to access polysubstituted 2-amino-1,3-thiazoles,” Tetrahedron, vol. 67, no. 26, pp. 4897–4904, 2011. View at Google Scholar
  27. K. Kundu and S. K. Nayak, “(±)-Camphor-10-sulfonic acid catalyzed direct one-pot three-component Mannich type reaction of alkyl (hetero)aryl ketones under solvent-free conditions: application to the synthesis of aminochromans,” RSC Advances, vol. 2, no. 2, pp. 480–486, 2012. View at Publisher · View at Google Scholar · View at Scopus
  28. A. Srivastava, S. Singh, and S. Samanta, “(±)-CSA catalyzed Friedel-Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3-indolylisoindolin-1-ones bearing a quaternary α-amino acid moiety,” Tetrahedron Letters, vol. 54, no. 11, pp. 1444–1448, 2013. View at Publisher · View at Google Scholar
  29. X. Jiang, Z. Song, C. Xu, Q. Yao, and A. Zhang, “(D,L)-10-camphorsulfonic-acid-catalysed synthesis of diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes from 2-hydroxychalcones and naphthol derivatives,” European Journal of Organic Chemistry, vol. 2014, no. 2, pp. 418–425, 2014. View at Publisher · View at Google Scholar
  30. D. A. Engel, S. S. Lopez, and G. B. Dudley, “Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones,” Tetrahedron, vol. 64, no. 29, pp. 6988–6996, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. N. Paul, M. Murugavel, S. Muthusubramanian, and D. Sriram, “Camphorsulfonic acid catalysed facile tandem double Friedlander annulation protocol for the synthesis of phenoxy linked bisquinoline derivatives and discovery of antitubercular agents,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 4, pp. 1643–1648, 2012. View at Publisher · View at Google Scholar · View at Scopus
  32. P. V. Shinde, A. H. Kategaonkar, B. B. Shingate, and M. S. Shingare, “An organocatalyzed facile and rapid access to α-hydroxy and α-amino phosphonates under conventional/ultrasound technique,” Tetrahedron Letters, vol. 52, no. 22, pp. 2889–2892, 2011. View at Publisher · View at Google Scholar · View at Scopus
  33. S. N. R. Mule, S. K. Battula, G. Velespula, D. R. Guda, and H. B. Ballikolla, “10-Camphorsulfonic acid ((±)-CSA) catalyzed facile one-pot synthesis of a new class of 2,5-disubstituted 1,3,4-oxadiazoles,” RSC Advances, vol. 4, no. 102, pp. 58397–58403, 2014. View at Publisher · View at Google Scholar
  34. B. K. Gorityala, S. Cai, J. Ma, and X.-W. Liu, “(S)-camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides,” Bioorganic & Medicinal Chemistry Letters, vol. 19, no. 11, pp. 3093–3095, 2009. View at Publisher · View at Google Scholar · View at Scopus
  35. S. S. Ali, S. Nasreen, M. Farooqui, S. H. Quadri, and S. Sultan, “Facile synthesis of coumarin under solvent-free condition,” International Journal of Research in Pharmaceutical and Biomedical Sciences, vol. 2, no. 3, pp. 1229–1231, 2011. View at Google Scholar
  36. A. Srivastava, S. M. Mobin, and S. Samanta, “(±)-CSA catalyzed one-pot synthesis of 6,7-dihydrospiro[indole-3,1′-isoindoline]-2,3′,4(1H,5H)-trione derivatives: easy access of spirooxindoles and ibophyllidine-like alkaloids,” Tetrahedron Letters, vol. 55, no. 11, pp. 1863–1867, 2014. View at Publisher · View at Google Scholar · View at Scopus
  37. W.-M. Dai, J. Wu, K. C. Fong, M. Y. H. Lee, and C. W. Lau, “Regioselective synthesis of acyclic cis-enediynes via an acid-catalyzed rearrangement of 1,2-dialkynylallyl alcohols. Syntheses, computational calculations, and mechanism,” Journal of Organic Chemistry, vol. 64, no. 14, pp. 5062–5082, 1999. View at Publisher · View at Google Scholar · View at Scopus
  38. R. M. Kellogg, J. W. Nieuwenhuijzen, K. Pouwer et al., “Dutch resolution: separation of enantiomers with families of resolving agents. A status report,” Synthesis, no. 10, pp. 1626–1638, 2003. View at Google Scholar · View at Scopus
  39. M. Vinatoru, E. Bartha, F. Badea, and J. L. Luche, “Sonochemical and thermal redox reactions of triphenylmethane and triphenylmethyl carbinol in nitrobenzene,” Ultrasonics Sonochemistry, vol. 5, no. 1, pp. 27–31, 1998. View at Publisher · View at Google Scholar · View at Scopus
  40. H. Zeng, H. Li, and H. Shao, “One-pot three-component Mannich-type reactions using Sulfamic acid catalyst under ultrasound irradiation,” Ultrasonics Sonochemistry, vol. 16, no. 6, pp. 758–762, 2009. View at Publisher · View at Google Scholar · View at Scopus
  41. J. Safari and Z. Zarnegar, “Ultrasound mediation for one-pot multi-component synthesis of amidoalkyl naphthols using new magnetic nanoparticles modified by ionic liquids,” Ultrasonics Sonochemistry, vol. 21, no. 3, pp. 1132–1139, 2014. View at Publisher · View at Google Scholar · View at Scopus
  42. E. Pelit and Z. Turgut, “Three-component aza-Diels-Alder reactions using Yb(OTf)3 catalyst under conventional/ultrasonic techniques,” Ultrasonics Sonochemistry, vol. 21, no. 4, pp. 1600–1607, 2014. View at Publisher · View at Google Scholar · View at Scopus
  43. C. Dong, K. Sanjay, and M. Ackmez, Handbook on Applications of Ultrasound Sonochemistry for Sustainability, CRC Press, Taylor & Francis Group, Boca Raton, Fla, USA, 2012.
  44. T. J. Mason and D. Peters, “Practical Sonochemistry,” in Power Ultrasound Uses and Applications, Ellis Horwood, New York, NY, USA, 2002. View at Google Scholar
  45. T. J. Mason, “Sonochemistry and the environment—providing a ‘green’ link between chemistry, physics and engineering,” Ultrasonics Sonochemistry, vol. 14, no. 4, pp. 476–483, 2007. View at Publisher · View at Google Scholar · View at Scopus
  46. J. L. Luche, Synthetic Organic Sonochemistry, Plenum Press, New York, NY, USA, 1998.
  47. J.-T. Li, S.-X. Wang, G.-F. Chen, and T.-S. Li, “Some applications of ultrasound irradiation in organic synthesis,” Current Organic Synthesis, vol. 2, no. 3, pp. 415–436, 2005. View at Publisher · View at Google Scholar · View at Scopus
  48. R. Gallardo-Macias and K. Nakayama, “Tin(II) compounds as catalysts for the Kabachnik-fields reaction under solvent-free conditions: facile synthesis of α-aminophosphonates,” Synthesis, no. 1, pp. 57–62, 2010. View at Publisher · View at Google Scholar · View at Scopus
  49. M. Adib, E. Sheibani, M. Mostofi, K. Ghanbary, and H. R. Bijanzadeh, “Efficient highly diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines,” Tetrahedron, vol. 62, no. 14, pp. 3435–3438, 2006. View at Publisher · View at Google Scholar · View at Scopus
  50. T. Kurz, “Synthesis of novel pyrido[2,3-e][1,3]oxazines,” Tetrahedron, vol. 61, no. 12, pp. 3091–3096, 2005. View at Publisher · View at Google Scholar · View at Scopus
  51. P. Zhang, E. A. Terefenko, A. Fensome, J. Wrobel, R. Winneker, and Z. Zhang, “Novel 6-aryl-1,4-dihydrobenzo[d] and oxazine-2-thiones as potent, selective, and orally active nonsteroidal progesterone receptor agonists,” Bioorganic & Medicial Chemistry Letters, vol. 13, no. 7, pp. 1313–1316, 2003. View at Publisher · View at Google Scholar
  52. H. Van de Poel, G. Guilaumet, and M. C. Viaud-Massuard, “Synthesis of 6,7,8,9-tetrahydropyrido[2,3-b]indolizine and 3,4-dihydro-2H-pyrido[2′,3′:4,5]pyrrolo[2,1-b][1,3]oxazine derivatives as new melatonin receptor ligands,” Tetrahedron Letters, vol. 43, no. 7, pp. 1205–1208, 2002. View at Publisher · View at Google Scholar
  53. S. Wang, Y. Li, Y. Liu, A. Lu, and Q. You, “Novel hexacyclic camptothecin derivatives. Part 1. Synthesis and cytotoxicity of camptothecins with an A-ring fused 1,3-oxazine ring,” Bioorganic & Medicinal Chemistry Letters, vol. 18, no. 14, pp. 4095–4097, 2008. View at Publisher · View at Google Scholar · View at Scopus
  54. S.-H. Zhao, J. Berger, R. D. Clark et al., “3,4-Dihydro-2H-benzo[1,4]oxazine derivatives as 5-HT6 receptor antagonists,” Bioorganic & Medicinal Chemistry Letters, vol. 17, no. 12, pp. 3504–3507, 2007. View at Publisher · View at Google Scholar · View at Scopus
  55. Y. Tabuchi, Y. Ando, H. Kanemura et al., “Preparation of novel (Z)-4-ylidenebenzo[b]furo[3,2-d][1,3]oxazines and their biological activity,” Bioorganic & Medicinal Chemistry, vol. 17, no. 11, pp. 3959–3967, 2009. View at Publisher · View at Google Scholar · View at Scopus
  56. N. Zanatta, A. M. C. Squizani, L. Fantinel et al., “Synthesis of N-substituted 6-trifluoromethyl-1,3-oxazinanes,” Journal of the Brazilian Chemical Society, vol. 16, no. 6, pp. 1255–1261, 2005. View at Publisher · View at Google Scholar · View at Scopus
  57. J. N. Joyce, S. Presgraves, L. Renish et al., “Neuroprotective effects of the novel D3/D2 receptor agonist and antiparkinson agent, S32504, in vitro against 1-methyl-4-phenylpyridinium (MPP+) and in vivo against 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP): a comparison to ropinirole,” Experimental Neurology, vol. 184, no. 1, pp. 393–407, 2003. View at Publisher · View at Google Scholar
  58. F. A. J. Kerdesky, “A novel and efficient method for the conversion of a trans-hexahydronaphthoxazine to a cis-isomer using boron tribromide,” Tetrahedron Letters, vol. 46, no. 10, pp. 1711–1712, 2005. View at Publisher · View at Google Scholar · View at Scopus
  59. C. Cimarelli, A. Mazzanti, G. Palmieri, and E. Volpini, “Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation,” Journal of Organic Chemistry, vol. 66, no. 14, pp. 4759–4765, 2001. View at Publisher · View at Google Scholar · View at Scopus
  60. M. Heydenreich, A. Koch, S. Klod, I. Szatmári, F. Fülöp, and E. Kleinpeter, “Synthesis and conformational analysis of naphth[1′,2′:5,6][1,3]oxazino[3,2-c][1,3]benzoxazine and naphth[1′,2′:5,6][1,3]oxazino[3,4-c][1,3]benzoxazine derivatives,” Tetrahedron, vol. 62, no. 48, pp. 11081–11089, 2006. View at Publisher · View at Google Scholar · View at Scopus
  61. R. Csütörtöki, I. Szatmári, A. Koch, M. Heydenreich, E. Kleinpeter, and F. Fülöp, “Synthesis and conformational analysis of new naphth[1,2-e][1,3]oxazino[3,4-c]quinazoline derivatives,” Tetrahedron, vol. 67, no. 44, pp. 8564–8571, 2011. View at Publisher · View at Google Scholar · View at Scopus
  62. R. Csütörtöki, I. Szatmári, M. Heydenreich et al., “Novel piperidine-fused benzoxazino-and quinazolinonaphthoxazines—synthesis and conformational study,” Tetrahedron, vol. 68, no. 31, pp. 6284–6288, 2012. View at Publisher · View at Google Scholar · View at Scopus
  63. Z. Turgut, E. Pelit, and A. Köycü, “Synthesis of New 1,3-Disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines,” Molecules, vol. 12, no. 3, pp. 345–352, 2007. View at Publisher · View at Google Scholar · View at Scopus
  64. H. Cao, H.-F. Jiang, C.-R. Qi, W.-J. Yao, and H.-J. Chen, “Brønsted acid-promoted domino reactions: a novel one-pot three-component synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines,” Tetrahedron Letters, vol. 50, no. 11, pp. 1209–1214, 2009. View at Publisher · View at Google Scholar · View at Scopus
  65. V. D. Dhakane, S. S. Gholap, U. P. Deshmukh, H. V. Chavan, and B. P. Bandgar, “An efficient and green method for the synthesis of [1,3]oxazine derivatives catalyzed by thiamine hydrochloride (VB1) in water,” Comptes Rendus Chimie, vol. 17, no. 5, pp. 431–436, 2014. View at Publisher · View at Google Scholar · View at Scopus
  66. T. Sun, Q. Cai, M. Li et al., “Facile diastereoselective synthesis of cis-perfluoroalkylated fused [1,3]oxazines from aromatic aldehydes, methyl perfluoroalk-2-ynoates and quinolines,” Tetrahedron, vol. 71, no. 4, pp. 622–629, 2015. View at Publisher · View at Google Scholar · View at Scopus
  67. S. Fiorito, S. Genovese, V. A. Taddeo, and F. Epifano, “Microwave-assisted synthesis of coumarin-3-carboxylic acids under ytterbium triflate catalysis,” Tetrahedron Letters, vol. 56, no. 19, pp. 2434–2436, 2015. View at Publisher · View at Google Scholar · View at Scopus
  68. A. A. Pereira, P. P. de Castro, A. C. de Mello, B. R. V. Ferreira, M. N. Eberlin, and G. W. Amarante, “Brønsted acid catalyzed azlactone ring opening by nucleophiles,” Tetrahedron, vol. 70, no. 20, pp. 3271–3275, 2014. View at Publisher · View at Google Scholar · View at Scopus
  69. Y. Chen, W. Shan, M. Lei, and L. Hu, “Thiamine hydrochloride (VB1) as an efficient promoter for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones,” Tetrahedron Letters, vol. 53, no. 44, pp. 5923–5925, 2012. View at Publisher · View at Google Scholar · View at Scopus
  70. M. Vafaeezadeh and H. Alinezhad, “Brønsted acidic ionic liquids: green catalysts for essential organic reactions,” Journal of Molecular Liquids, vol. 218, no. 1, pp. 95–105, 2016. View at Publisher · View at Google Scholar