Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4'-[4'H]chroman]-2-ones

Ionic liquid mediated synthesis of novel heterocyclic compounds 1-[(1H-benzoimidazol-2-yl)amino]-2'-phenylspiro[azetidine- 4,4'-[4'H]chroman]-2-ones (3) and 1-[(1H-benzoimidazol-2-yl)amino]- 3-chloro-2'-phenylspiro[aze tidine-4,4'-[4'H] chroman]-2-ones (4) was accomplished by condensing substituted 2-hydrazino benzimidazole (1), flavanone (2), and acetyl chloride/chloroacetyl chloride in ionic liquid, [bmim]PF6 with or without using catalyst in excellent yield (90%--95%). Further, compounds 3 and 4 were acylated with trifluoroacetic anhydride to give N-acylated products (5 and 10); 3 when treated with HCHO and (C2H5)2NH gave Mannich bases (6) and with aldehydes afforded 3-arylidene-2-azetidinone (7). Compounds 4 underwent nucleophilic substitution with (i) KI (Finkelstein reaction) and (ii) phenols to give the corresponding iodo and phenoxy derivatives (8 and 9). The synthesized compounds were characterized by analytical and spectral (IR, 1 H NMR, 13C NMR, and HRMS) data and evaluated for insecticidal activity against Periplaneta americana using cypermethrin as standard and found to exhibit excellent results.

Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4 -[4 H ]chroman]-2-ones

Ionic liquid mediated synthesis of novel heterocyclic compounds 1-[(1H-benzoimidazol-2-yl)amino]-2'-phenylspiro[azetidine- 4,4'-[4'H]chroman]-2-ones (3) and 1-[(1H-benzoimidazol-2-yl)amino]- 3-chloro-2'-phenylspiro[aze tidine-4,4'-[4'H] chroman]-2-ones (4) was accomplished by condensing substituted 2-hydrazino benzimidazole (1), flavanone (2), and acetyl chloride/chloroacetyl chloride in ionic liquid, [bmim]PF6 with or without using catalyst in excellent yield (90%--95%). Further, compounds 3 and 4 were acylated with trifluoroacetic anhydride to give N-acylated products (5 and 10); 3 when treated with HCHO and (C2H5)2NH gave Mannich bases (6) and with aldehydes afforded 3-arylidene-2-azetidinone (7). Compounds 4 underwent nucleophilic substitution with (i) KI (Finkelstein reaction) and (ii) phenols to give the corresponding iodo and phenoxy derivatives (8 and 9). The synthesized compounds were characterized by analytical and spectral (IR, 1 H NMR, 13C NMR, and HRMS) data and evaluated for insecticidal activity against Periplaneta americana using cypermethrin as standard and found to exhibit excellent results.

___

  • Joshi, K. C.; Jain R.; Dandia, A.; Sharma, K. J. Fluorine Chem. 1992, 56, 1–27.
  • Sharma, K. Asian J. Chem. Rev. 1994, 5, 8–40.
  • Goudgaon, N.M.; Basha, N.J. J. Indian Chem. Soc. 2010, 87, 987–992.
  • Akula, G.; Srinivas, B.; Vidyasagar, M.; Kandikonda S. Int. J. Pharm. Tech. Res. 2011, 3, 360–364.
  • Gill, C.; Jadhav, G.; Shaikh, M.; Kale, R.; Ghawalkar, A.; Nagargoje, D.; Shiradkar, M. Bioorg. Med. Chem. Lett. 2008, 18 , 6244–6247.
  • Coon, T.; Moree, W. J.; Li, B.; Yu, J.; Zamani Kord, S.; Malany, S.; Santos, M. A.; Hernandez, L. M.; Petroski, R. E.; Sun, A.; Wen, J.; Sullivan, S.; Haelewyn, J.; Hedrick M.; Hoare, S. J.; Bradbury, M. J.; Crowe, P. D.; Beaton, G. Bioorg. Med. Chem. Lett. 2009, 19, 4380–4384.
  • Refaat, H. M. Eur. J. Med. Chem. 2010, 45, 2949–2956.
  • Miller, J. F.; Turner, E. M.; Gudmundsson, K. S.; Jenkinson, S.; Spaltenstein, A.; Thomson, M.; Wheelan, P. Bioorg. Med. Chem. Lett. 2010, 20, 2125–2128.
  • Rathee, P. S.; Dhankar, R.; Bhardwaj, S.; Gupta, M.; Kumar, R. J. Applied Pharm. Sci. 2011, 1, 127–130.
  • Kulmagambetova, E. A.; Yamovoi, V. I.; Kusainova, D. D.; Pak R. N.; Kulyyatov, A. T.; Turdybekov, K. M.; Adekenov, S. M.; Gatilov Y. V. Chem. Nat. Compd. 2002, 38, 527–531. 11 Pannala, A. S; Chan, T. S.; O’Brien, P. J.; Rice-Evans, C. A. Biochem. Biophys. Res. Commun. 2001, 282, 1161–1168.
  • Cushnie, T. P.; Lamb, A. J. Int. J. Antimicrob. Agents 2006, 27, 181.
  • Basile, A.; Giordano, S.; L´ opez-S´ aez, J. A.; Cobianchi, R. C. Phytochemistry 1999, 52, 1479–1482.
  • Harborne, J. B.; Baxter, H. The Hand Book of Natural Flavonoids, John Wiley, Chichester, NY, 1999.
  • Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988–4035.
  • Mehta, P. D.; Sengar, N. P. S.; Pathak, A. K. Eur. J. Med. Chem. 2010, 45, 5541–5560.
  • Sharma, R.; Samadhiya, P.; Srivastava, S. D.; Srivastava, S. K. Org. Commun. 2011, 4, 42–51.
  • Patel, N. B.; Patel, J. C. J. Med. Chem. Res. 2011, 20, 511–521.
  • Ilango, K.; Arunkumar, S. Trop. J. Pharm. Res. 2011, 10, 219–229.
  • Vijay Kumar, M. M. J.; Nagaraja, T. S.; Sameer, H.; Jayachandran, E.; Sreenivasa, G. M. J. Pharm. Sci. Res. 2009, 1, 83–92.
  • Welton, T. Chem. Rev. 1999, 99, 2071–2084.
  • Van, R. F.; Sheldon, R. A. Chem. Rev. 2007, 107, 2757–2785.
  • Sharma, K.; Jain. R. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 2086–2095.
  • Sareen, V.; Khatri, V.; Jain, P.; Sharma, K. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 140–146.
  • Jain, R.; Sharma, K.; Kumar, D. Tetrahedron Lett. 2012, 53, 1993–1997.
  • Jain, R.; Sharma, K.; Kumar, D. Tetrahedron Lett. 2012, 53, 6236–6240.
  • Galletti, P.; Quintavalla, A.; Ventrici, C.; Giannini, G.; Cabri, W.; Giacommi, D. New J. Chem. 2010, 34, 2861– 28
  • Feroci, M.; Chiarotta, I.; Orsini, M.; Sotgiu, G.; Inesi, A. Adv. Synth. Catal. 2008, 350, 1355–1359.
  • Chen, R.; Yang, B.; Su, W. Synt. Commun. 2006, 36, 3167–3174.
  • Laurila, M. L.; Magnus, N. A.; Staszak, M. A. Org. Process Res. Dev. 2009, 13, 1199–1201.
  • Agarwal, R.; Agarwal, C.; Singh, C.; Mishra, V. S. Indian J. Chem. 1989, 28B, 893–896.
  • Elliot, M.; Farnham, A.; Janes, N. F.; Johnson, D. M; Pullman, D. A. Pestic. Sci. 1980, 11, 513–525.
  • Shay, P. N.; Lionel, E. W. C; Fung, Y. P.; Yan, H.; Manjunatha, R. K.; Shuit, H. H. Pestic. Sci. 1998, 54, 261–268. Bednyagina, N. P.; Postovoski, I. Y.; Zhur. Obschei. Khim. 1960, 30, 1431–1437.
  • Gautam N.; Chourasia O. P. Indian J. Chem. 2012, 51B, 1020–1026.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Application of experimental design on determination of aluminum content in saline samples by adsorptive cathodic stripping voltammetry

Sinan YILMAZ, Betül ÖZTÜRK, Durmuş ÖZDEMİR

Removal of Cr(III) and Cu(II) using poly(2-chloroaniline)/polyvinylidene uoride composite cation-exchange membranes by Donnan dialysis

Tuğba Sardohan KÖSEOĞLU, Esengül KIR, Sabriye Perçin ÖZKORUCUKLU, Esin KARAMIZRAK

New synthetic methodology for construction of the 3,4-dihydroquinolin-2-one skeleton

Çağatay DENGİZ, Metin BALCI

Synthesis and characterization of thermally stable camphor-based polyimide--clay nanocomposites

Murat YİĞİT, Turgay SEÇKİN, Beyhan YİĞİT, Süleyman KÖYTEPE

Synthesis and evaluation of acetylcholineesterase inhibitory potential and antioxidant activity of benzothiazine derivatives

Durre SHAHWAR, Uzma SANA, Naeem AHMAD

Study on crystal transformation process of magnesium carbonate hydrate based on salt lake magnesium resource utilization

Juan DU, Zhen CHEN, Yu-long WU, Ming-de YANG

Removal of Cr(III) and Cu(II) using oly(2-chloroaniline)/polyvinylidenefluoride composite cation-exchange membranes by Donnan dialysis

Esengül KIR, Sabriye Perçin ÖZKORUCUKLU

An efficient ligand-free method for the transfer hydrogenation of ketones and aldehydes catalyzed by different complexes

Sedat YAŞAR, Suzan ÇEKİRDEK, Nilay Akkuş TAŞ

Synthesis and antimicrobial investigation of some 5H-pyridazino[4,5-b]indoles

İlker AVAN, Alaattin GÜVEN, Kıymet GÜVEN

Ionic liquid mediated synthesis, reactions, and insecticidal activity of 1-[(1H-benzoimidazol-2-yl)amino]spiro[azetidine-4,4'-[4'H]chroman]-2-ones

Kanti SHARMA, Renuka JAIN