Facile synthesis of 5-bromotropono[c]-fused pyrazoles and isoxazole

A facile synthesis of a series of new 5-bromotropono[c]pyrazole derivatives (3 and 10--15) as well as 5-bromotropono[c]isoxazole (17) is described, involving a condensation reaction of 3-acetyl-5-bromotropolone (1) with hydrazine monohydrate (2), arylhydrazine hydrochlorides (4--9), and hydroxylamine hydrochloride (16), respectively. All the synthesized compounds were obtained in good yields of 56%--77% and their structures were characterized by spectral data and HRMS.

Facile synthesis of 5-bromotropono[c]-fused pyrazoles and isoxazole

A facile synthesis of a series of new 5-bromotropono[c]pyrazole derivatives (3 and 10--15) as well as 5-bromotropono[c]isoxazole (17) is described, involving a condensation reaction of 3-acetyl-5-bromotropolone (1) with hydrazine monohydrate (2), arylhydrazine hydrochlorides (4--9), and hydroxylamine hydrochloride (16), respectively. All the synthesized compounds were obtained in good yields of 56%--77% and their structures were characterized by spectral data and HRMS.

___

  • Genin, M. J.; Biles, C.; Keiser, B. J.; Poppe, S. M.; Swaney, S. M.; Tarpley, W. G.; Yagi, Y.; Romero, D. L. J. Med. Chem. 2000, 43, 1034–1040.
  • Fustero, S.; S´ anchez-Rosell´ o, M.; Barrio, P.; Sim´ on-Fuentes, A. Chem. Rev. 2011, 111, 6984–7034.
  • Barreiro, E. J.; Camara, C. A.; Verli, H.; Brazil-M´ as, L.; Castro, N. G.; Cintra, W. M.; Aracava, Y.; Rodrigues, C. R.; Fraga, C. A. M. J. Med. Chem. 2003, 46, 1144–1152.
  • Adamo, M. F. A.; Duffy, E. F.; Donati, D.; Sarti-Fantoni, P. Tetrahedron 2007, 63, 2684–2688.
  • Rashad, A. E.; Hegab, M. I.; Abdel-Megeid, R. E.; Micky, J. A.; Abdel-Megeid, F. M. E. Bioorg. Med. Chem. 2008, 16, 7102–7106.
  • Via, L. D.; Marini, A. M.; Salerno, S.; Motta, C. L.; Condello, M.; Arancia, G.; Agostinelli, E.; Toninello, A. Bioorg. Med. Chem. 2009, 17, 326–336.
  • Mekheimer, R. A.; Ahmed, E. A.; Sadek, K. U. Tetrahedron 2012, 68, 1637–1667.
  • Dodiya, K.; Trivedi, D. R.; Kataria, A. B.; Shah, V. H. Curr. Org. Chem. 2012, 16, 400–418.
  • Huang, Y.-Y.; Wang, L.-Y.; Chang, C.-H.; Kuo, Y.-H.; Kaneko, K.; Takayama, H.; Kimura, M.; Juang, S. H.; Wong, F. F. Tetrahedron 2012, 68, 9658–9664.
  • Lavecchia, G.; Berteina-Raboin, S.; Guillaumet, G. Tetrahedron Lett. 2004, 45, 2389–2392.
  • Mali, J. R.; Pratap, U. R.; Jawale, D. V.; Mane, R. A. Tetrahedron Lett. 2004, 51, 3980–3982.
  • Kumar, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2009, 74, 7046–7051.
  • Sales, Z. S.; Mani, N. S. J. Org. Chem. 2009, 74, 891–894.
  • Chandrasekhar, S.; Rajaiah, G.; Srihari, P. Tetrahedron Lett. 2001, 42, 6599–6601.
  • Deng, B. L.; Zhao, Y.; Hartman, T. L.; Watson, K.; Buckheit Jr., R. W.; Pannecouque, C.; Clercq, E. D.; Cushman, M. Eur. J. Med. Chem. 2009, 44, 1210–1214.
  • Santos, M. M. M.; Faria, N.; Iley, J.; Coles, S. J.; Hursthouse, M. B.; Martins, M. L.; Moreira R. Bioorg. Med. Chem. Lett. 2010, 20, 193–195.
  • Srinivas, A.; Nagaraj, A.; Reddy, C. S. Eur. J. Med. Chem. 2010, 45, 2353–2358.
  • Chao, E. Y.; Minick, D. J.; Sternbach, D. D.; Shearer, B. G.; Collins, J. L. Org. Lett. 2002, 4, 323–326. Kivrak, A.; Larock, R. C. J. Org. Chem. 2010, 75, 7381–7387.
  • El-Badri, M. H.; Kurth, M. J. J. Comb. Chem. 2009, 11, 228–238.
  • Seephonkai, P.; Isaka, M.; Kittakoop, P.; Trakulnaleamsai, S.; Rattanajak, R.; Tanticharoen, M.; Thebtaranonth, Y. J. Antibiot. 2001, 54, 751–752.
  • Bourderioux, A.; B´ en´ eteau, V.; M´ erour, J.-Y.; Baldeyrou, B.; Ballot, C.; Lansiaux, A.; Bailly, C.; Gu´ evel, R. L.; Guillouzo, C.; Routier, S. Org. Biomol. Chem. 2008, 6, 2108–2117.
  • Katz, J. D.; Jewell, J. P.; Guerin, D. J.; Lim, J.; Dinsmore, C. J.; Deshmukh, S. V.; Pan, B.-S.; Marshall, C. G.; Lu, W.; Altman, M. D. et al. J. Med. Chem. 2011, 54, 4092–4108.
  • Mesa-Siverio, D.; Est´ evez-Braun, A.; Ravelo, ´ A. G.; Murguia, J. R.; Rodr´ıguez-Afonso, A. Eur. J. Org. Chem. 2003, 4243–4247.
  • Wahlstr¨ om, N.; Stensland, B.; Bergman, J. Tetrahedron 2004, 60, 2147–2153.
  • Cavazza, M.; Guella, G.; Pietra, F. Tetrahedron 2000, 56, 1917–1922.
  • Bourderioux, A.; Routier, S.; B´ en´ eteau, V.; M´ erour, J. Y. Tetrahedron 2007, 63, 9465–9475.
  • Azizian, J.; Ramazani, A.; Haji, M. HeIv. Chim. Acta 2011, 94, 371–375.
  • Zhang, L. C.; Imafuku, K. J. Heterocycl. Chem. 1991, 28, 717–720.
  • Dolle, R. E.; Nelson, K. H., Jr. J. Comb. Chem. 1999, 1, 235–282.
  • Li, Y.; Gao, W. T. Beilstein J. Org. Chem. 2010, 6, 966–972.
  • Li, Y.; Zhang, C. H.; Sun, M. C.; Gao, W. T. J. Heterocycl. Chem. 2009, 46, 1190–1194.
  • Li, Y.; Yan, Y.; Gao, W. T. Heterocycles 2012, 85, 421–429.
  • Li, Y.; Sun, M. C.; Gao, W. T. J. Heterocycl. Chem. 2012, 49, 167–172.
  • Li, Y.; Gao, W. T. Heterocycles 2010, 81, 2617–2623.
  • Li, Y.; Chang, M. Q.; Liu, R.; Lin, G. H.; Gao, W. T. Res. Chem. Intermed. 2013, 9, 2621–2627.
  • Piao, M. Z.; Imafuku, K. J. Heterocycl. Chem. 1996, 33, 389–398.
  • Chang, M. Q.; Li, Y.; Gao, W. T. Heterocycles 2011, 83, 1631–1640.
  • Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737–6740.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Investigation of the adsorption kinetics of methylene blue onto cotton wastes

Bilal ACEMİOĞLU, Murat ERTAŞ, Mehmet Hakkı ALMA, Mustafa USTA

In vitro effects of pesticide exposure on the activity of the paraoxonase-1 enzyme from sheep liver microsomes

Büşra Koncuk CEBECİ, Zuhal ALIM, Şükrü BEYDEMİR

Crystal growth morphology of magnesium hydroxide

Jian-Song WU, Juan DU, Yi-Min GAO

The chemistry concerned with the sonochemical-assisted synthesis of CeO2/poly(amic acid) nanocomposites

Shiva YAZDANI, Mehdi HATAMI, Seyed Mohammad VAHDAT

Deposition and characterization of Cu9S5 nanocrystals from unsymmetrical [(Hex)(Me)NC(S)NC(O)C6H3(NO2)2-3,5]2Cu(II) and [(Et)(Bu)NC(S)NC(O)C6H4-4-NO2]2Cu(II) complexes by colloidal thermolysis method

Sohail SAEED, Rizwan HUSSAIN

Solvent extraction of praseodymium(III) from acidic nitrate medium using Cyanex 921 and Cyanex 923 as extractants in kerosene

Nandita PANDA, Nihar Bala DEVI, Sujata MISHRA

Selective oxidation of sulfides and hydrocarbons with H2O2 over manganese catalyst supported on nanoparticles

Massomeh GHORBANLOO, Roghayeh TARASI

Te(II)-induced heterocyclization of 1,2-alkadienephosphonates

Dobromir Dimitrov ENCHEV

Spectroscopic investigation and oxidation of the anticholinergic drug atropine sulfate monohydrate by hexacyanoferrate(III) in aqueous alkaline media: a mechanistic approach

Manjunath METI, Sharanappa NANDIBEWOOR, Shivamurti CHIMATADAR

Facile synthesis of 5-bromotropono[c]-fused pyrazoles and isoxazole

Yang LI, Liangyu XU, Wentao GAO