Hydroxyapatite Catalyzed Cyclization of Aryl Enones: Solvent-Free Efficient Synthesis of Some 4-Aryl-5,6-Dihydro-6-(Substituted Phenyl)-4H-1,3-Oxazine-2-Amines

Ganesamoorthy Thirunarayanan

Abstract


Some 4-aryl-5,6-dihydro-6-(substituted phenyl)-4H-1,3-oxazine- 2-amine derivatives including 4-(4-methyl-1-naphthyl)-5,6- dihydro-6-(substituted phenyl)-4H-1,3-oxazine-2-amines have been synthesised by hydroxyapatite catalyzed solvent-free cyclization of aryl chalcones and urea using microwave irradiation under solventfree condition. The yields of the oxazines were more than 85%. The synthesised oxazine amines have been characterized by their physical constants, analytical and spectroscopic data.

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J. Cherian, I. Choi, A. Nayyar, U.H. Manjunatha, T. Mukherjee, Y.S. Lee, H.I. Boshoff, R. Singh,Y. H. Ha, M. Goodwin, S.B. Lakshminarayana, P. Niyomrattanakit, J. Jiricek, R. Ravindran, T. Dick, T.H. Keller, V. Dartois, C.E. Barry, J. Med. Chem., 54(16), 5639 (2011).

A.M. Thompson, H.S. Sutherl , D.B. Palmer, I. Kmentova, A. Blaser, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma, W.A. Denny, J. Med. Chem., 54(16), 6563, (2011).

I.P. Yakovlev, A.V. Prep’yalov, B.A. Ivin, Chem. Heterocycl. Compd, 30(3), 255, (1994).

M.K. Manjula, K.M.L. Rai, S.L. Gaonkar, K.A. Raveesha S. Satish, Eur. J. Med. Chem., 44, 280 (2009).

B.P. Mathew, A. Kumar, S. Sharma, P.K. Shukla, M. Nath, Eur. J. Med. Chem. 45, 1502, (2010).

M.J. Elarfi, H.A. Al-Difar, Sci. Rev.Chem. Commun., 2(2), 103, (2012).

V. Tiwari, J. Meshram, P. Ali, J. Sheikh U. Tripathi, J. Enzyme Inhibit.Med. Chem., 26(4), 569, (2011).

B.C. Das, A.V. Madhukumar, J. Anguiano S. Mani, Bioorg. Med. Chem. Lett., 19(15), 4204, (2009).

D. Zhou, B.L. Harrison, U. Shah, T.H. Andree, G.A. Hornby, R. Scerni, Bioorg. Med. Chem. Lett., 16(5), 1338,(2006).

S. Wang, Y. Li, Y. Liu, A. Lu Q. You, Bioorg. Med. Chem. Lett., 18(14), 4095, (2008).

Y. Ando, K. Ando, M. Yamaguchi, J. Kunitomo, M. Koida, R. Fukuyama, Bioorg. Med. Chem. Lett., 16(22), 5849, (2006).

L. Benameur, Z. Bouaziz, P. Nebois, M. H. Bartoli, M. Boitard, H. Fillion, Chem. Pharm. Bulletin (Tokyo), 44(3), 605, (1996).

K. Roy, I. Mitra A. Saha, Chem. Biol. Drug Design, 74(5), 507, (2009).

A. Blaser, D. Palmer, S. H. Sutherl , I. Kmentova, S. G. Franzblau B. Wan, J. Med.Chem., 55(1), 312, (2012).

L. Seal, D. Von Hoff. R. Lawrence, E. Izbicka R.M. Jamison, Investi. New Drugs, 15(4), 289, (1997).

B. Brudeli, L.R. Moltzau, K.W. Andressen, K.A. Krobert, J. Klaveness F.O. Levy, Bioorg. Med. Chem., 18(24), 8600, (2010).

M. Akhter, A. Husain, N. Akhter M.S.Y. Khan, Indian J. Pharm. Sci., 73, 101, (2011).

D. Gothi, J.M. Joshi, Recent Patent. Antiinfect. Drug Discov., 6(1), 27, (2011).

K.S. Oh. S. Lee, J.K. Choi B.H. Lee, Comb. Chem. Higher Throughput Screen, 13(9), 790 (2010).

S.Y. Cho, J.Y. Baek, S.S. Han. S.K. Kang, J.D. Ha J.H. Ahn, Bioorg. Med. Chem. Lett., 16(3), 499, (2006).

S.F. Lee, Q. Vérolet A. Fürstenberg, Angew. Chem. Int. Ed., 52(34), 8948, (2013).

L.A. Kass, Biotech Histochem, 70(1), 19, (1995).

L.A. Kass, Biotech Histochem, 70(1), 29,(1995).

C. Jung, B.K. Müller, D.C. Lamb, F. Nolde, K. Müllen C. Bräuchle, J. Am.Chem. Soc., 128(15), 5238, (2006).

A.K. Verma, D. Chioudhary, R.K. Saunthwal, V. Rustagi, M. Patel R.K. Tiwari, J. Org. Chem., 78(13), 6657, (2013).

M.A. Khalilzadeh, I. Yavari, Z. Hossaini H. Sadeghifar, Monatsch Chem., 140, 467, (2009).

S.B. Sapkal, K.F. Shelke, A.H. Kategaonkar M.S. Shingare, Green Chem. Lett., 2(2), 57, (2009).

J.H. MacMillan S.S. Washburne, Detailed Synthetic Procedure for 4-(4-bromophenyl)-1,3(3H) Oxazine-2,6-Dione related 4 5-aryl substituted -1,3(3H) Oxazine-2,6-Diones. Spectroscopic analytical data are included. Temple University, http://www.archive.org. (2013).

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

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

M. Subramanian, G. Vanangamudi G. Thirunarayanan, Spectrochim. Acta Part A, 110, 116, (2013).

Z. Turgut, E. Pelit A. Koycil, Molecules, 12, 345, (2007).

M. Ansari, S. M. Naghib, F. Moztarzadeh A. Salati, Ceramics-Silikáty, 55, 123, (2011).

G. Thirunarayanan, Int. J. Sci. Res. Know, 1, 580, (2013).




DOI: http://dx.doi.org/10.2478/umcschem-2013-0015
Date of publication: 2015-05-23 17:08:45
Date of submission: 2015-04-30 12:17:42


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