Microwave Assisted Selective Synthesis of four Chromanones Via Biscyclization Method in the Presence of Polyphosphoric Acid and Crystal Structure Determination of Their Dicarboxylic Acids

Document Type : Research Article


1 Faculty of Chemistry, Teacher Training University, P.O. BOX 15614, Tehran, I.R. IRAN

2 Department of Chemistry, Imam Hossein University, Tehran, I.R. IRAN


Microwave irradiation is used in the synthesis of four tricyclic chromanones 11-14. The chromanone 14 and 12 are selectively formed thermally and under microwave in the presence of polyphosphoric acid (PPA) from the same dicarboxylic acid 9, respectively. The crystal structures of the two diacids are also reported. The corresponding ortho and meta isomers of diacids crystallize in the space group Pbca of the orthorhombic system and C2/c of the monoclinic system respectively, with 8 and 4 molecules in the unit cells of dimensions a = 4.9955(1) Å and 4.8092(4) Å; b = 19.177(4) Å and 11.5609(1) Å; c = 25.885(5) Å and 21.247(2) Å; α = 90˚ and β = 91.214(3)˚ respectively. The structures have been refined to final values for the crystallographic R factors of 0.0401 and 0.0247, based on 2146 and 1030 observed independent reflections, respectively.


Main Subjects

[1] Koch, K. and Biggers, M. S., J. Org. Chem. (1994), 59, 1216; (b) Lockhart, I. M., In Chromanes, Chromenes and Chromones, Ed. Ellis, G.P., John Wiley, (1997).
[2] Shockravi,  A.  and   Moradi,  K.  S.,   MSc.   Thesis, Teacher Training University, (1999).
[3] Kelly, T. R., Chandsakumar, N. S. and Saha, J. K., J. Org. Chem., 54, 980 (1989).
[4] Reitsch, F. C., Schrmitz, C. and Aubru, J. M., Tetrahedron Lett., 32, 3845 (1991); ibid,  Rossekelly, T.,  29, 3545 (1988).
[5] Christopfel, W. C. and Miller, L. L. J., Org. Chem., 49, 5198 (1984).
[6] Shockravi, A. and Bruce, J. M., J. Sci. I. R. Iran., 7, 21 (1996).
[7] Shockravi, A. and Jahanbin Sardrudi, H., Iran. J. Chem. & Chem. Eng., 18, 24 (1999).
[8] Shockravi, A. and Kodaean, S. M., Teacher Training University, J. Science,  2 (3&4) p. 67 (2003).
[9] Camps, F., Coll, J., Messeguer, A., Pericas, M. A., Ricart, S., Bowers, W. S. and Soderlund, D. M., Synthesis, 725 (1980).
[10] Sato, K., Lin, Y. S. and Amakasu, T., Bull. Chem. Soc. Jpn., 42, 2600 (1969).
[11] Subramanian, R. S. and Balasubamanian, K. K., J. Chem. Soc. Chem. Commun., 1469 (1990).
[12] Mingos, D. M. P. and Baghurst, D. R., Chem. Soc.  Rev., 20, 1 (1991).
[13] Gabriel, C., Gabriel, S., Grant, E. H., Halstead, B. S. J. and Mingos, D. M. P., Chem. Soc. Rev., 27, 213 (1998).
[14] Caddik, S., Chem. Soc. Rev., 16, 10404 (1995).
[15] (a)Bruker  (1998a)  SAINT+,  Program  for  data reduction and correction, ver. 6.01; Bruker Axs, Madison, Wisconsin, USA; (b) Bruker (1998b) SMART,Bruker molecular analysisresearch tool, ver.5.059; Bruker Axs,   Madison, Wisconsin, USA; (c) Sheldrick,G. M. (1998a), SADABS ,Bruker/ Siemens area detector absorption   correction program, ver.2.01; Bruker Axs, Madison, Wisconsin, USA; (d) Sheldrick, G.M.(1998b), SHELXTL,Structure determination software suite, ver.5.10; Bruker Axs, Madison, Wisconsin, USA.
[16] Lynch, D. E., Smith, G., Byriel, K. A. and Kennard, C.H. L., Aust. J. Chem.,51, 1019 (1998).
[17] Leiserowitz, L., Acta Crystallogr. Sect. B, 32, 775 (1976).
[18] Rheingold, A. L., Baldacchini, C. J. and Grote, C. W., J. Crystallogr. Spectrosc. Res., 19, 25 (1989).
[19] Frankenbach, G. M., Britton, D. and Etter, M. C., Acta Crystallogr. Sect.C., 47, 553 (1991).