Synthesis of new oxindole derivatives containing benzothiazole and thiazolidinone moieties using nano silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (NSB-DBU) as catalyst

A facile one-pot synthesis of novel oxindole derivatives bearing benzothiazolylmethyl-2-thioxothiazolidin-4-one was accomplished via one-pot reaction of 5-oxoindolinylidene rhodanine-3-acetic acid derivatives, 2-aminothiophenol, and triphenyl phosphite in the presence of tetrabutylammonium bromide (TBAB) and nano silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (NSB-DBU) as heterogeneous reusable nanocatalyst. The target compounds were obtained in excellent yields (85%--92%) and short reaction times under fairly mild reaction conditions.

Synthesis of new oxindole derivatives containing benzothiazole and thiazolidinone moieties using nano silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (NSB-DBU) as catalyst

A facile one-pot synthesis of novel oxindole derivatives bearing benzothiazolylmethyl-2-thioxothiazolidin-4-one was accomplished via one-pot reaction of 5-oxoindolinylidene rhodanine-3-acetic acid derivatives, 2-aminothiophenol, and triphenyl phosphite in the presence of tetrabutylammonium bromide (TBAB) and nano silica-bonded 5-n-propyl-octahydro-pyrimido[1,2-a]azepinium chloride (NSB-DBU) as heterogeneous reusable nanocatalyst. The target compounds were obtained in excellent yields (85%--92%) and short reaction times under fairly mild reaction conditions.

___

  • Lesyk, R. B.; Zimenkovsky, B. S. Curr. Org. Chem. 2004, 8, 1547–1577.
  • Tomasic, T.; Masic, L. P. Curr. Med. Chem. 2009, 16, 1596–1629.
  • Lesyk, R.; Zimenkovsky, B.; Atamanyuk, D.; Jensen, F.; Kie´c-Kononowicz, K.; Gzella, A. Bioorg. Med. Chem. 2006, 14, 5230–5240.
  • Havrylyuk, D.; Zimenkovsky, B.; Vasylenko, O.; Zaprutko, L.; Gzella, A.; Lesyk, R. Eur. J. Med. Chem. 2009, 44, 1396–1404.
  • Rydzik, E.; Szadowska, A.; Kaminska, A. Acta Pol. Pharm. 1984, 41, 459–464.
  • Samir, B.; Wesam, K.; Fadda, A. A. Eur. J. Med. Chem. 2007, 42, 948–954.
  • Elbarbary, A. A.; Khodair, A. I.; Pedersen, E. B.; Nielsen, C. Monatsh. Chem. 1994, 125, 593–598.
  • Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Bossa, R.; Chiericozzi, M.; Galatulas, I.; Salvatore, G. Eur.
  • J. Med. Chem. 1996, 31, 383–387.
  • Andreani, A.; Rambaldi, M.; Locatelli, A.; Leoni, A.; Bossa, R.; Chiericozzi, M.; Galatulas, I.; Salvatore, G. Eur.
  • J. Med. Chem. 1993, 28, 825–829. 10.Ohishi, Y.; Mukai, T.; Nagahara, M.; Yajima, M.; Kajikawa, N.; Miyahara, K.; Takano, T. Chem. Pharm. Bull.
  • Catal. Sci. Technol. 2013, 3, 2717–2722. 27.Taki, B. S. G.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Rostami, M.;
  • Baidya, M.; Mayr, H. Chem. Commun. 2008, 2008, 1792–1794.
  • Ying, A. G.; Liu, L.; Wu, G. F.; Chen, G.; Chen, X. Z.; Ye, W. D. Tetrahedron Lett. 2009, 50, 1653–1657.
  • Baharfar, R.; Shariati, N. Aust. J. Chem. 2014, DOI 10.1071/CH13712.
  • Baharfar, R.; Shariati, N. C. R. Chimie 2014, 17, 413–419. 37.Shariati, N.; Baharfar, R. J. Chin. Chem. Soc. 2014, 61, 337–340.
  • Baharfar, R.; Baghbanian, S. M.; Vahdat, S. M. Tetrahedron Lett. 2011, 52, 6018–6020.
  • Qiu, H.; Jiang, Q.; Wei, Z.; Wang, X.; Liu, X.; Jiang, S. J. Chromatogr. A 2007, 1163, 63–69.
  • Pardasani, R. T.; Pardasani, P.; Jain, A.; Kohli, S. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 1569–1575.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Selective CO methanation over NiO--Al_2O_3--ZrO_2 and Co_3O_4--Al_2O_3--ZrO_2 catalysts

Filiz DEREKAYA, Derya ERMERGEN

Ring opening and ring closure reactions of chromone-3-carboxylic acid: unexpected routes to synthesize functionalized benzoxocinones and heteroannulated pyranochromenes

Magdy Ahmed IBRAHIM, Tarik El-sayed ALI

Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors

MEHDI RIMAZ, PARIA POURHOSSEIN, BEHZAD KHALILI

The synthesis of 1,3-dialkyl-4-methylimidazolinium salts and their application in palladium catalyzed Heck coupling reactions

Murat YİĞİT, Gülin BAYAM, Beyhan YİĞİT, İsmail ÖZDEMİR

Revisiting the biodesulfurization capability of hyperthermophilic archaeon Sulfolobus solfataricus P2 revealed DBT consumption by the organism in an oil/water two-phase liquid system at high temperatures

GÖKHAN GÜN, YUDA YÜRÜM, GİZEM DİNLER DOĞANAY

Gaseous and dissolved oxygen sensing with stabilized pyrene in ionic liquid modified electrospun slides

Özlem ÖTER, Gülhan Sabanci ŞAHİN

HPLC fluorescence determination of ochratoxin A utilizing a double internal standard and its application to poultry feed

Muzaffer TUNÇEL, Elif Mine Öncü KAYA, Ülkü Dilek UYSAL, Tufan GÜRAY

Synthesis and electrochemistry of phthalocyanines bearing [(3,4-dimethoxybenzyl)oxy] groups

İpek ÖMEROĞLU, Zekeriya BIYIKLIOĞLU

PFAM catalyzed enantioselective diethylzinc addition to imines

Özdemir DOĞAN, Eda ÇAĞLI

Synthesis and biological evaluation of new pyridines containing imidazole moiety as antimicrobial and anticancer agents

İkhlass ABBAS, Sobhi GOMHA, Mahmoud ELAASSER, Mohammed BAUOMI