Aqueous phase fly-ash catalyzed [4+2] Diels-Alder reaction of aryl enones and cyclopentadiene: Synthesis and insect antifeedant activities of aryl bicyclo [2.2.1] heptene-2-yl-methanones

Ganesamoorthy Thirunarayanan

Abstract


A series containing ten aryl 3-(substituted phenyl) bicyclo [2.2.1] heptene-2-yl-methanone derivatives including 3- (substituted phenyl) bicyclo [2.2.1]hepten-2-yl-(pyren-1-yl)- methanones have been synthesized by aqueous phase fly-ash catalyzed [4+2] Diels-Alder cyclo addition reaction of cyclopentadiene and aryl chalcones. The yields of the methanones are more than 60%. The synthesized methanones are characterized by their physical constants and spectral data. The insect antifeedant activities of synthesized methanones have been studied using Dethler’s leaf-discs bioassay method.

Full Text:

PDF

References


E.B. Mubofu, J.B.F.N. Engberts, J. Phys. Org. Chem., 17, 180, (2004).

G. Arena, R. Cali, V. Cucinotta, S. Musumeci, E. Rizzarelli, S. Sammartano, J. Chem. Soc. Dalton Trans., 1271 (1983).

R. Breslow, U. Marita and D.C. Tetrahedron. Lett., 24, 1901, (1983).

R. Breslow, U. Marita, Tetrahedron Lett., 25, 1239, (1984).

S. Otto, F. Bertoncin, J.B.F.N. Engberts, J. Am. Chem. Soc., 118, 7702, (1996).

S. Otto, J.B.F.N. Engberts, J. Am. Chem. Soc., 121, 6798, (1999).

F. Fringuelli, O. Piermatti, F. Pizzo, L. Vaccaro, Eur. J. Org. Chem., 3, 439, (2001).

A.J. Boersma, B. Bruin, B.L. Feringa, G. Roelfes, Chem. Commun., 48, 2394, (2012).

A. Boersma, B.L. Feringa, G. Roelfes, Org. Lett., 9, 3647, (2007).

D.C. Rideout, R. Breslow, J. Am. Chem. Soc., 102, 7816, (1980).

S. Otto, J.B.F.N. Engberts, Tetrahedron Lett., 36, 2645, (1995).

R.P. Megens, G. Roefes, Chem. Eur. J., 17, 8514, (2011).

Q. Jin, L. Zhang, H. Cao, T. Wang, X. Zhu, J. Jiang, M. Liu, Langmuir., 27, 13847, (2011).

G. Roelfes, A.J. Boersma, B.L. Feringa, Chem. Commun., 635, (2006).

C.H. Kuo, C.M. Niemeyer, L. Fruk, Croat. Chem. Acta., 84, 269, (2011).

N.S. Oltra, G. Roelfes, Chem. Commun., 6039 (2008).

S. Otto, J.B.F.N. Engberts, J.C.T. Kwak, J. Am. Chem. Soc., 120, 9517, (1998).

D.L. Boger, A.R. Lerner, B.F. Cravatt, J. Org. Chem., 59, 5078, (1994).

G. Thirunarayanan, G. Vanangamudi, V. Sathiyendiran, K. Ravi, Indian J. Chem., 50B, 593, (2011).

G. Thirunarayanan, G. Vanangamudi, M. Subramanian, Org. Chem. An Indian J., 9, 1, (2013).

G. Thirunarayanan, G. Vanangamudi, Spectrochim. Acta., 81A, 390, (2011).

G. Thirunarayanan, S. Surya, S. Srinivasan, G. Vanangamudi, V. Sathiyendiran, Spectrochim. Acta., 75A, 152, (2010).

G. Thirunarayanan, J. Indian Chem. Soc., 85, 447, (2008).

G. Thirunarayanan, Iup. J. Chem., 3(4), 35, (2010).

G. Thirunarayanan, P. Mayavel, Thirumurthy, Spectrochim. Acta., 91A, 18, (2012).

Dethler’s, VG (1947) Chemical Insect Attractants and Repellents, Blackistan, Philadelphia,p. 210.

M. Gopalakrishnan, P. Sureshkumar, V. Kanagarajan, J. Thanusu, Res. Chem. Intermed., 33(6), 541, (2007).

D. El-Mogazi, D.J. Lisk, L.K. Weinstein, Sci. Total Environ., 74, 1, (1988).




DOI: http://dx.doi.org/10.2478/umcschem-2013-0014
Date of publication: 2015-05-23 17:08:45
Date of submission: 2015-04-30 12:02:25


Statistics


Total abstract view - 807
Downloads (from 2020-06-17) - PDF - 545

Indicators



Refbacks

  • There are currently no refbacks.


Copyright (c) 2015 Annales Universitatis Mariae Curie-Sklodowska, sectio AA – Chemia