A two-component protocol for synthesis of 3-(2-(substituted phenylamino)thiazol-4-yl)-2H-chromen-2-ones

An efficient 2-component synthesis of a series of 3-(2-(substituted phenylamino)thiazol-4-yl)-2H-chromen-2-ones (3a--j) was achieved by the reaction of 3-(2-thiocyanatoacetyl)-2H-chromen-2-one (1) with a variety of suitably substituted anilines in 1:1 molar ratio in ethanol. The structures of the products were established by elemental analyses, and UV-vis, FTIR, 1H and 13C NMR, and mass spectroscopy. 3-(2-(4-Methylphenylamino)thiazol-4-yl)-2H-chromen-2-one (3j) was further characterized by single crystal X-ray diffraction study. This compound, C19H14N2OS, crystallizes in the orthorhombic space group Pna21, with Z = 4, and unit cell parameters a = 13.0785(11), b = 25.746(2), c = 4.7235(3) Å, a = b = g = 90°.

A two-component protocol for synthesis of 3-(2-(substituted phenylamino)thiazol-4-yl)-2H-chromen-2-ones

An efficient 2-component synthesis of a series of 3-(2-(substituted phenylamino)thiazol-4-yl)-2H-chromen-2-ones (3a--j) was achieved by the reaction of 3-(2-thiocyanatoacetyl)-2H-chromen-2-one (1) with a variety of suitably substituted anilines in 1:1 molar ratio in ethanol. The structures of the products were established by elemental analyses, and UV-vis, FTIR, 1H and 13C NMR, and mass spectroscopy. 3-(2-(4-Methylphenylamino)thiazol-4-yl)-2H-chromen-2-one (3j) was further characterized by single crystal X-ray diffraction study. This compound, C19H14N2OS, crystallizes in the orthorhombic space group Pna21, with Z = 4, and unit cell parameters a = 13.0785(11), b = 25.746(2), c = 4.7235(3) Å, a = b = g = 90°.

___

  • Wagner B. D. Molecules 2009, 14, 210–237.
  • Smyth, T.; Ramachandran, V. N.; Smyth, W. F. Int. J. Antimicrob. Agents. 2009, 33, 42–48.
  • Deki´ c, V.; Radulovi´ c, N.; Vukicevi´ c, R.; Deki´ c, B.; Stojanovi´ c-Radi, Z.; Pali´ c, R. Afr. J. Pharma. Pharmacol. 2011, 5, 371–375.
  • Belluti, F.; Fontana, G.; Bo, L. D.; Carenini, N.; Giommarelli, C.; Franco Zunino, F. Bioorg. Med. Chem. 2010, 18, 3543–3550.
  • Al-Soud, Y. A.; Al-Sa’doni, H. H.; Amajaour. H. A. S.; Salih, K. S. M.; Mubarak, M. S.; Al-Masoudi, N. A.; Jaber, I. H., Z. Naturforsch. 2008, 63b, 83–90.
  • Manvar, A.; Malde, A.; Verma, J.; Virsodia, V.; Mishra, A.; Upadhyay, K.; Acharya, H.; Coutinho, E.; Shah, Eur. J. Med. Chem. 2008, 43, 2395–2403.
  • Zhou, X.; Wang, X. B.; Wang, T.; Kong, L. Y. Bioorg. Med. Chem. 2008, 16, 8011–8021.
  • Edenharder, A.; Speth, C.; Decker, M.; Kolodziej, H.; Kayser, O.; Platt, K. L. Mutat. Res. 1995, 345, 57–62.
  • Lee, B. H.; Clothier, M. F.; Dutton, F. E.; Conder, G. A.; Johnson, S. S. J. Ethnopharmacol. 2005, 97, 293–299. Hoult, J. R. S.; Paydt, M. Gen. Pharmac. 1996, 27, 713–718.
  • Hwu, J. R.; Singha, R.; Hong, S. C.; Chang, Y. H.; Das, A. R.; Vliegen, I.; Clercq, E. D.; Neyts, J. Antiviral Res. 2008, 77, 157–162.
  • Kalkhambkar, R. G.; Kulkarni, G. M.; Kamanavalli, C. M.; Premkumar, N.; Asdaq, S. M. B.; Sun, C. M. Eur. J. Med. Chem. 2008, 43, 2178–2188.
  • Radanyi, C.; Bras, G. L.; Messaoudi, S.; Bouclier, C.; Peyrat, J. F.; Brion, J. D.; Marsaud, V.; Renoir, J. M.; Alami, M. Bioorg. Med. Chem. Lett. 2008, 18, 2495–2498.
  • Wood, W. J. L.; Patterson, A. W.; Tsuruoka, H.; Jain, K. R.; Ellman, J. A. J . Am. Chem. Soc. 2005, 127, 15521–15529.
  • Starcevic, S.; Kocbek, P.; Hribar, K. G.; Rizner, T. L.; Gobec, S. Chem. Biol. Interact. 2011, 191, 60–65.
  • Cheng, J. F.; Ishikawa, A.; Ono, Y.; Arrhenius, T.; Nadzan, A. Bioorg. Med. Chem. Lett. 2003, 13, 3647–3650.
  • Chimenti, F.; Secci, D.; Bolasco, A.; Chimenti, P.; Granese, A.; Befani, O.; Turini, P.; Alcaroc, S.; Ortuso, F. Bioorg. Med. Chem. Lett. 2004, 14, 3697–3703.
  • Raj, H. G.; Parmar, V. S.; Jain, S. C.; Goel, S.; Poonam.; Himanshu.; Malhotra, S.; Singh, A.; Olsen, C. E.; Wengeld, J. Bioorg. Med. Chem. 1998, 6, 833–839.
  • Sarojini, B. K.; Krishna, B. G.; Darshanraj, C. G.; Bharath, B. R.; Manjunatha, H. J. Eur. Med. Chem. 2010, 45, 3490–3496.
  • Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Bossa, R.; Chiericozzi, M.; Galatulas, I.; Salvator, G. J. Eur. Med. Chem. 1996, 31, 383–387.
  • El-Gaby, M. S. A. J. Chin. Chem. Soc.-Taip. 2004, 51, 125–132.
  • Clemence, F.; Marter, O. L.; Delevalle, F.; Benzoni, J.; Jouanen, A.; Jouquey, S.; Mouren, M.; Deraedt, R. J. Med. Chem. 1988, 31, 1453–1461.
  • Dawane, B. S.; Konda, S. G. Int. J. Pharm. Sci. Rev. Res. 2010, 3(2), 96–98.
  • Abdel-Aziz, H. A.; Abdal-Wahab, B. F.; El-Sharief, M. A. S. S.; Abdulla, M. M. Monatsh. Chem. 2009, 140, 431–437.
  • Plouvier, B.; Houssin, R.; Hecquet, B.; Colson, P.; Houssier, C.; Waring, M. J.; Henichart, J. P; Bailly, C. Bioconjugate Chem. 1994, 5, 475–482.
  • Patt, W. C.; Hamilton, H. W.; Taylor, M. D.; Ryan, M. J.; Taylor, D. G. Jr.; Connolly, C. J. C.; Doharty, A. M.; Klutchko, S. R.; Sircar, I.; Steinbaugh, B. A. J. Med. Chem. 1992, 35, 2562–2570. Bell, F. W.; Cantrell, A. S.; Hoberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordon, C. L.; Kinnick, M. D.; Lind, P.; Morin, J. M. Jr.; Noreen, R. J. Med. Chem. 1995, 38, 4929–4937.
  • Kalkhambkar, R. G.; Kulkarni, G. M.; Shivkumar, H.; Rao, R. N. Eur. J. Med. Chem. 2007, 42, 1272–1276.
  • Vijesh, A. M.; Isloor, A. M.; Prabhu, V.; Ahmad, S.; Malladi, S. Eur. J. Med. Chem. 2010, 45, 5460–5464.
  • Rudolph, J.; Theis, H.; Hanke, R.; Endermann, R.; Johannsen, L.; Geschke, F. U. J. Med. Chem. 2001, 44, 619–625.
  • Geronikaki, A.; Hadjipavlov-Litina, D.; Zablotskaya, A.; Segal, I. Bioinorg. Chem. Appl. 2007, Article ID 92145, 7 pages doi:10.1155/2007/92145.
  • Fink, B. A.; Mortensen, D. S.; Stauffer, S. R.; Aron, Z. D.; Katzenellenbogen, J. A. Chem. Biol. 1999, 6, 205–209. Muijlwijk-Koezen, J. Ev.; Timmerman, H.; Vollinga, R. C.; Von Drabbe Kunzel, J. F.; De Groote, M.; Visser, S.; Ijzerman, A. P. J. Med. Chem. 2001, 44, 749–754.
  • Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719–3727.
  • Wagner, B. D. Molecules 2009, 14, 210–237.
  • Kaloyanova, S; Ivanova, I; Tchorbanov, A; Dimitrova, P; Deligeorgiev, T. J. Photochem. Photobiol. B . 2011, 103, 215–221.
  • Flaˇ s´ık, R; Stankoviˇ cov´ a, H; G´ aplovsk´ y, A; Donovalov´ a, J. Molecules 2009, 14, 4838–4848.
  • Lim, N. C.; Schuster, J. V.; Porto, M. C.; Tanudra, M. A.; Yao, L.; Freake, H. C.; Br¨ uckner, C. Inor. Chem. 2005, 44, 2018–2027.
  • Hara, K.; Sato, T.; Katoh, R.; Furube, A.; Ohga, Y.; Shinpo, A.; Suga, S.; Sayama, K.; Sugihara, H.; Arakawa, H. J. Phys. Chem. B 2003, 107, 597–603.
  • Mills, J. T.; Gleeson, H. F.; Goodby, J. W.; Hird, M.; Seed, A. J. Mater. Chem. 1998, 8, 2385–2390.
  • Dear, K. M.; Bedfordshire, L.; Jeffreys, R. A.; Thomas, D. A. 3,630,738. US, 1971.
  • Nebe-von-Caron, G.; Stephens, P. J.; Hewitt, C. J.; Powell, J. R.; Badley, R. A. J. Microbiol Meth. 2000, 42, 97–114.
  • Rye, H. S.; Yue, S.; Wemmer, D. E.; Quesada, M. A.; Haugland, R. A.; Mathies, R. A.; Glazer, A. N. Nucleic Acids Res. 1992, 20, 2803–2812.
  • Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030–16039.
  • Koti, R. J.; Koloavi, G. D.; Hegde, V. S.; Khazi, I. M. Syn. Comun., 2007, 37, 99–105. Full crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-867181. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data request/cif.or by e-mailing data request@ ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
  • Blessing, R. H. Acta Cryst. 1995, A51, 33–38.
  • Spek, A. L. J. Appl. Cryst. 2003, 36, 7–13.
  • Sheldrick, G. M. Acta Cryst. 2008, A64, 112–122.
  • Donovalov´ a, J.; Cig´ aˇ n, M.; Stankoviˇ cov´ a, H.; Gaˇ spar, J.; Danko, M.; G´ aplovsk´ y, A.; Hrdloviˇ c, P. Molecules 2012, 17, 3259–3276.
  • Yao, H.; Domoto, K.; Isohashi, T.; Kimura, K. Langmuir 2005, 21, 1067–1073.
  • Garc´ıa-B´ aez, E. V.; Mart´ınez-Mart´ınez, F. J.; H¨ opfl, H.; Padilla-Mart´ınez, I. I. ARKIVOC 2003, xi, 100–111.
  • Lee, S. H.; Helal, A.; Kim, H. S. Bull. Korean. Chem. Soc. 2010, 31, 615–619.
  • Yanxi, S.; Zhen, C.; Hongqi, L. Curr. Org. Chem. 2012, 16, 2690–2707.
  • Helal, A.; Harun-Or-Rashid, M.; Choi, C. H.; Kim, H. S. Tetrahedron 2011, 67, 2794–2802.
  • Mizukami, S.; Okada, S.; Kimura, S.; Kikuchi, K. Inorg. Chem. 2009, 48, 7630–7638. Lin, W.; Yuan, L.; Cao, X.; Tan, W.; Feng, Y. Eur. J. Org. Chem. 2008, 2008 (29), 4981–4987.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

A phthalocyanine - fluorescein conjugate

Vefa AHSEN, Yunus ZORLU, İlker ÜN, Fabienne DUMOULIN, Hanife İBİŞ O ĞLU

Theoretical study on the addition reaction between propadienylidene and methyleneimine

Mengyuan WANG, Yungang CHEN, Shanshan DING, Yingde WANG

Synthesis, spectroscopic characterization, and genotoxicity of a new group of azo-oxime metal chelates

Beyza CABİR, Barış AVAR, Mehmet GÜLCAN, Ahmet KAYRALDIZ

Environmentally green synthesis of thioformamide derivatives

Ali RAMAZANI, Sang Woo JOO, Fatemeh Zeinali NASRABADI

Exploring distinct binding site regions of b2-adrenergic receptor via coarse-grained molecular dynamics simulations

Sibel ÇAKAN, Ebru Demet AKDOĞAN

Potentiometric study of equilibrium constants of a novel triazine--thione derivative and its stability constants with Hg2+, Cu2+, Ni2+, Pb2+, and Zn2+ metal ions in ethanol and water mixed

Fatih POLAT, Hasan ATABEY, Hayati SARI, Alaaddin ÇUKUROVALI

A phthalocyanine--fluorescein conjugate

İlker ÜN, Yunus ZORLU, Hanife İBİŞOĞLU, Fabienne DUMOULIN

Adsorption equilibrium of water vapor on activated carbon and alumina and carbon and alumina impregnated with hygroscopic salt

Ioan SOLOMON, Ana M. RIBEIRO, João C. SANTOS, José M. LOUREIRO

Exploring distinct binding site regions of $beta_2$-adrenergic receptor via coarse-grained molecular dynamics simulations

Ebru Demet AKDO GAN, Sibel ÇAKAN

Spectral, electrochemical, luminescence, and dye-sensitized solar cell studies of mono and d-f hetero binuclear cryptates

Arunachalam VIJAYARAJ, Raju PRABU, Ranganathan SURESH, Subbaiah MANOHARAN