Isoquinoline-substituted triazole and pyran derivatives: synthesis andcomputational studies

Isoquinoline-substituted triazole and pyran derivatives: synthesis andcomputational studies

The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazoles from isoquinoline-substituted homopropargylalcohol backbone is described (42%{88% yields). A ring closing metathesis reaction and an intramolecular Pauson{Khandreaction of enyne system derived from a homopropargyl alcohol backbone to afford the corresponding isoquinoline-substituted dihydropyran and cyclopentenone-pyran, respectively, are also described (54% and 78% yields). Informationabout the structural, electronic, and physico-chemical properties of the novel compounds, obtained by density functionaltheory application, is also reported.

___

  • 1.Welsch, M. E.; Snyder, S. A.; Stockwell, B. R.Curr. Opin. Chem. Biol.2010,14, 347-361.
  • 2.Michael, J. P.Nat. Prod. Rep.2008,25, 166-187.
  • 3.Solomon, V. R.; Lee, H.Curr. Med. Chem.2011,18, 1488-1508.
  • 4.Couch, G. D.; Burke, P. J.; Knox, R. J.; Moody, C. J.Tetrahedron2008,64, 2816-2823.
  • 5.Fryatt, T.; Pettersson, H. I.; Gardipee, W. T.; Bray, K. C.; Green, S. J.; Slawin, A. M. Z.; Beall, H. D.; Moody,C.J. Bioorg. Med. Chem.2004,12, 1667-1687.
  • 6.Hughes, G.; Bryce, M. R.J. Mater. Chem.2005,15, 94-107.
  • 7.Zhang, W.; Hu, J.; Young, D. J.; Hor, T. S. A.Organometallics2011,30, 2137-2143.
  • 8.Bentley, K. W.The Isoquinoline Alkaloids; Hardwood Academic: Amsterdam, the Netherlands, 1998; Vol. 1.
  • 9.Kletsas, D.; Li, W.; Han, Z.; Papadopoulos, V.Biochem. Pharmacol.2004,67, 1927-1932.
  • 10.Mach, U. R.; Hackling, A. E.; Perachon, S.; Ferry, S.; Wermuth, C. G.; Schwartz, J. C.; Sokoloff, P.; Stark, H.ChemBioChem2004,5, 508-518.
  • 11.Muscarella, D. E.; O'Brain, K. A.; Lemley, A. T.; Bloom, S. E.Toxicol. Sci.2003,74, 66-73.
  • 12.Dzierszinski, F.; Coppin, A.; Mortuaire, M.; Dewally, E.; Slomianny, C.; Ameisen, J. C.; DeBels, F.; Tomavo, S.Antimicrob. Agents Chemother.2002,46, 3197-3207.
  • 13.Polt, R.Amaryllidaceae Alkaloids with Antitumor Activity. In Organic Synthesis, Theory and Applications;Hudlicky, T., Ed.; JAI Press: Greenwich, CT, USA, 1996; Vol. 3, p 109.
  • 14.Whipple, G. H.Angiology1977,28, 737-749.
  • 15.Luo, L. J. Chin.J. Med.1955,41, 452-455.
  • 16.Kong, W.; Wei, J.; Abidi, P.; Lin, M.; Inaba, S.; Li, C.; Wang, Y.; Wang, Z.; Si, S.; Pan, H.; et al.Nat. Med.2004,10, 1344-1351.
  • 17.Durola, F.; Sauvage, J. P.; Wenger, O. S.Chem. Commun.2006, 171-173.
  • 18.Sweetman, B. A.; Muller-Bunz, H.; Guiry, P. J.Tetrahedron Lett.2005,46, 4643-4646.
  • 19.Lim, C. W.; Tissot, O.; Mattison, A.; Hooper, M. W.; Brown, J. M.; Cowley, A. R.; Hulmes, D. I.; Blacker, A.J.Org. Process Res. Dev.2003,7, 379-384.
  • 20.Alcock, N. W.; Brown, J. M.; Hulmes, G. I.Tetrahedron: Asymmetry1993,4, 743-756.
  • 21.Liu, S. J.; Zhao, Q.; Chen, R. F.; Deng, Y.; Fan, Q. L.; Li, F. Y.; Wang, L. H.; Huang, C. H.; Huang, W.Chem.Eur. J.2006,12, 4351-4361.
  • 22.Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C.Inorg. Chem.2006,45, 6152-6160.
  • 23.Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.;Takiguchi, T.; Okada, S.; et al.J. Am. Chem. Soc.2003,125, 12971-12979.
  • 24.Esvaran, S.; Adhikari, A. V.; Shetty, N. S.Eur. J. Med. Chem.2009,44, 4637-4647.
  • 25.Kumar, S. S.; Kavitha, H. P.Mini-Rev. Org. Chem.2013,10, 40-65.
  • 26.Radhika, C.; Venkatesham, A.; Sarangapani, M.Med. Chem. Res.2012,21, 3509-3513.
  • 27.Chaudhary, P. M.; Chavan, S. R.; Shirazi, F.; Razdan, M.; Nimkar, P.; Maybhate, S. P.; Likhite, A. P.; Gonnade,R.; Hazara, B. G.; Deshpande, S. R.Bioorg. Med. Chem. Lett.2009,17, 2433-2440.
  • 28.Zhou, J. P.; Zhang, H. B.; Qian, H.; Lin, L.; Huang, W. L.; Ni, S. J.Lett. Drug Design Discov.2009,6, 181-185.
  • 29.Thomas, K. D.; Adhikari, A. V.; Shetty, N. S.Eur. J. Med. Chem.2010, 45, 3803-3810.
  • 30.Holla, B. S.; Mahalinga, M.; Karthikeyan, M. S.; Poojary, B.; Akberali, P. M.; Kumari, N. S.Eur. J. Med. Chem.2005,40, 1173-1178.
  • 31.Sumangala, V.; Poojary, B.; Chidananda, N.; Fernandes, J.; Kumari, N. S.Arch. Pharm. Res.2010,33, 1911-1918.
  • 32.Thomas, K. D.; Adhikari, A. V.; Chowdhury, I. H.; Sumesh, E.; Pal, N. K.Eur. J. Med. Chem.2011,46, 2503-2512.
  • 33.Kategaonkar, A. H.; Shinde, P. V.; Kategaonkar, A. H.; Pasale, S. K.; Shingate, B. B.; Shingare, M. S.Eur. J.Med. Chem.2010,45, 3142-3146.
  • 34.Gupta, M.Bioorg. Med. Chem. Lett.2011,21, 4919-4923.
  • 35.Keshk, E. M.; El-Desoky, S. I.; Hammouda, M. A. A.; Abdel-Rahman, A. H.; Hegazi, A. G.Phosphorus, Sulfur,and Silicon2008,183, 1323-1343.
  • 36.Ozyank, M.; Demirci, S.; Bektas, H.; Demirbas, N.; Demirbas, A.; Karaoglu, S. A.Turk. J. Chem.2012,26,233-246.
  • 37.Corey, E. J.; Ghosh, A. K.Tetrahedron Lett.1987,28, 175-178.
  • 38.Polo, E.; Bellabarba, R. M.; Prini, G.; Traverso, O.; Green, M. L. H.J. Organomet. Chem.1999,577, 211-218.
  • 39.Hatanaka, M.; Himeda, Y.; Imashiro, R.J. Org. Chem.1994,59, 111-119.
  • 40.Sakai, A.; Aoyama, T.; Shioiri, T.Tetrahedron Lett.2000,41, 6859-6863.
  • 41.Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.J. Chem. Soc., Perkin Trans. 11973, 975-977.
  • 42.Schore, N. E. InComprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon: Oxford, UK, 1995;Vol. 12, p 703.
  • 43.Geis, O.; Schmalz, H. G.Angew. Chem., Int. Ed.1998,37, 911-914.
  • 44.Jeong, N. InTransition Metals in Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany,1998; Vol. 1, p 560.
  • 45.Brummond, K. M.; Kent, J. L.Tetrahedron2000,56, 3263-3283.
  • 46.Bonaga, L. V. R.; Krafft, M. E.Tetrahedron2004,60, 9795-9833.
  • 47.Schore, N. E.; Croudace, M. C.J. Org. Chem.1981,46, 5436-5438.
  • 48.Exon, C.; Magnus, P.J. Am. Chem. Soc.1983,105, 2477-2478.
  • 49.Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M.Synlett1999, 771-773.
  • 50.Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C.Angew. Chem., Int. Ed.1997,36, 2801-2804.
  • 51.Blanco-Urgoiti, J.; Casarrubios, L.; Dominguez, G.; Perez-Castells, J.Tetrahedron Lett.2002,43, 5763-5765.
  • 52.Krafft, M. E.; Bonaga, L. V. R.; Hirosawa, C.J. Org. Chem.2002,67, 1233-1246.
  • 53.Gumus, A.; Ucur, S.Heterocycl. Commun.2014,20, 361-364.
  • 54.Buyukadal, N. N.; Seven, S.; Aslan, N.; Yenidede, D; Gumus, A.Tetrahedron: Asymmetry2015,26, 1285-1291.
  • 55.Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; der Eycken, E. V.Org. Lett.2004,6, 4223-4225.
  • 56.Taft, R.W.; Topsom, R.D.Prog. Phys. Org. Chem.1987,16, 1-83.
  • 57.Taft, R.W.Prog. Phys. Org. Chem.1983,14, 247-350.
  • 58.Taft, R.W.; Koppel, I. A.; Topsom, R. D.; Anivia, F.J. Am. Chem. Soc.1990,112, 2047-2052.
  • 59.Kohn, W.; Sham, L.J. Phys. Rev.1965,140, A1133-A1138.
  • 60.Larsen, A. H.; De Giovannini, U.; Whitenack, D. L.; Wasserman, A.; Rubio, A.J. Phys. Chem. Lett.2013,4,2734-2738.
  • 61.Becke, A.Phys. Rev. A: At., Mol., Opt. Phys.1988,38, 3098-3100.
  • 62.Vosko, S.; Wilk, L.; Nusair, M.Can. J. Phys.1980,58, 1200-1211.
  • 63.Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R.Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al. Gaussian, Inc., Wallingford, CT, USA,2009.
  • 64.Spartan 14, Wavefunction Inc., Irvine, CA, USA, 2014.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Preparation, characterization, and adsorption studies of core@shell SiO2@CeO2nanoparticles: a new candidate to remove Hg(II) from aqueous solutions

İbrahim KULA, Mehmet UĞURLU, Ali İmran VAİZOĞULLAR, Ahmet BALCI

ALIREZA KHATAEE, MURAT KIRANŞAN, SEMRA KARACA, SAMIRA AREFI- OSKOUI

Slawomir DOMAGALA, Slawomira SKRZYPEK, Michal CICHOMSKI, Andrzej LENIART

Electrochemical investigation of 2-[8-hydroxyquinoline-5-yl)azo]benzo[c]cinnolineon a platinum electrode in dimethysulfoxide

Zehra YAZAN, Esma KILIÇ, Emine KILIÇ, Öznur ÖLMEZ, Funda ÖZTÜRK

Synthesis and computational studies of new metallo-phthalocyanines bearingdibenzoxanthenes and evaluation of their optical properties in solution and solidPMMA/ZnPc/Al nanocomposite films

Ali Reza KARIMI, Zeinab JAFARZADEH, Meysam SOURINIA, Akbar ZENDEHNAM, Azam KHODADADI, Zeinab DALIRNASAB, Mohammad SOLIMANNEJAD, Peyman ZOLGHARNEIN

Zr(IV), Ti(IV), and V(III) complexes of some benzimidazole, benzothiazole, andbenzoxazole ligands: characterization and catalyst efficiency in ethylenepolymerization

Hamdi Ali ELAGAB, Helmut G. ALT

Ali Reza KARIMI, Zeinab JAFARZADEH, Meysam SOURINIA, Akbar ZENDEHNAM, Azam KHODADADI, Zeinab DALIRNASAB, Mohammad SOLIMANNEJAD, Peyman ZOLGHARNEIN

Funda ÖZTÜRK, Zehra YAZAN, Oznur OLMEZ, Emine KILIÇ, Esma KILIÇ

Kadir DOĞANAY, Ünzile KELEŞTEMUR, Sevgi BALCIOĞLU, Burhan ATEŞ, Aliye ALTUNDAŞ

Aouatef TABBI, Zafer Asim KAPLANCIKLI, Dahmane TEBBANI, Leyla YURTTAŞ, Zerrin CANTÜRK, Özlem ATLI, Merve BAYSAL, Gülhan Turan ZITOUNI