Aryl Chalcones as Efficient Precursors for Deriving Oxazine: Solvent-Free Synthesis and Antimicrobial Activities of some Oxazine-2-amines

Thirunarayanan, Ganesamoorthy; Sundararajan, R.; Arulkumaran, R.

doi:10.18052/www.scipress.com/ILCPA.23.82

ILCPA > ILCPA Volume 23 > Aryl Chalcones as Efficient Precursors for...

< Back to Volume

Aryl Chalcones as Efficient Precursors for Deriving Oxazine: Solvent-Free Synthesis and Antimicrobial Activities of some Oxazine-2-amines

Full Text PDF

Abstract:

A series of some oxazine derivatives has been synthesised by fly-ash:H2SO4 catalyzed solvent-free cyclization of aryl chalcones and urea under microwave irradiation. The yields of the oxazines were more than 85%. The synthesised oxazines were characterized by their physical constants, analytical and spectroscopic data. The antimicrobial activities of these oxazines have been studied using Bauer-Kirby method.

Info:

Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 23)

Pages:

82-97

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.23.82

Citation:

G. Thirunarayanan et al., "Aryl Chalcones as Efficient Precursors for Deriving Oxazine: Solvent-Free Synthesis and Antimicrobial Activities of some Oxazine-2-amines", International Letters of Chemistry, Physics and Astronomy, Vol. 23, pp. 82-97, 2014

Online since:

November 2013

Authors:

Ganesamoorthy Thirunarayanan, R. Sundararajan, R. Arulkumaran

Keywords:

Antimicrobial Activities, Chalcones, Environmentally Benign Reaction, Fly-Ash: H₂SO₄, Oxazine Amines

Export:

RIS, BibTeX, Text

Distribution:

Open Access

This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

I. P. Yakovlev, A. V. Prep'yalov, B. A. Ivin, Chem. Heterocycl. Compd. 30(3) (1994) 255-271.

M. K. Manjula, K. M. L. Rai, S. L. Gaonkar, K. A. Raveesha, S. Satish, Eur. J. Med. Chem. 44 (2009) 280-288.

B. P. Mathew, A. Kumar, S. Sharma, P. K. Shukla, M. Nath, Eur. J. med. Chem. 45 (2010) 1502-1507.

M. J. Elarfi, H. A. Al-Difar, Sci. Rev. Chem. Communn. 2(2) (2012) 103-107.

V. Tiwari, J. Meshram, P. Ali, J. Sheikh, U. Tripathi, J. Enzyme Inhib. Med. Chem. 26(4) (2011) 569-78.

B. C. Das, A. V. Madhukumar, J. Anguiano, S. Mani, Bioorg. Med. Chem. Lett. 19(15) (2009) 4204-4206.

D. Zhou, B. L. Harrison, U. Shah, T. H. Andree, G. A. Hornby, R. Scerni, Bioorg. Med. Chem. Lett. 16(5) (2006) 1338-1341.

S, Wang, Y. Li, Y. Liu, A. Lu, Q. You, Bioorg. Med. Chem. Lett. 18(14) (2008) 40954097.

Y. Ando, K. Ando, M. Yamaguchi, J. Kunitomo, M. Koida, R. Fukuyama, Bioorg. Med. Chem. Lett. 16(22) (2006) 5849-5854.

L. Bouaziz, P. Nebois, M. H. Bartoli, M. Boitard, H. Fillion, Chem. Pharm. Bull. 44(3) (1996) 605-608.

K. Roy, I. Mitra, A. Saha, Chem. Biol. Drug. Des. 74(5) (2009) 507-516.

A. Blaser, B. D. Palmer, H. S. Sutherland, I. Kmentova, S. G. Franzblau, B. Wan, J. Med. Chem. 55(1) (2012) 312-326.

L. Seal, D. Von Hoff, R. Lawrence, E. Izbicka, R. M. Invest. New Drugs. 15(4), (1997) 289-293.

B. Brudeli, L. R. Moltzau, K. W. Andressen, K. A. Krobert, J. Klaveness, F. O. Levy, Bioorg. Med. Chem. 18(24) (2010) 8600-8613.

M. Akhter, A. Husain, N. Akhter, M. S. Y. Khan, Indian J. Pharm. Sci. 73 (2011) 101- 104.

D. Gothi, J. M. Joshi, Recent Pat Antiinfect Drug Discov. 6(1) (2011) 27-37.

K. S. Oh, S. Lee, J. K. Choi, B. H. Lee, Comb. Chem. High. Throughput Screen. 13(9) (2010) 790-797.

S. Y. Cho, J. Y. Baek, S. S. Han, S. K. Kang, J. D. Ha, J. H. Ahn, Bioorg. Med. Chem. Lett. 16(3) (2006) 499-502.

S. F. Lee, Q. Vérolet, A. Fürstenberg, Angew. Chem. Inter. Ed. 52(34) (2013) 89488951.

L. A. Kass, Biotech Histochem. 70(1) (1995) 19-23.

L. A. Kass, Biotech Histochem. 70(1) (1995) 29-33.

C. Jung, B. K. Müller, D. C. Lamb, F. Nolde, K. Müllen, C. Bräuchle, J. Am. Chem. Soc. 128(15) (2006) 5283-5291.

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

A. K. Verma, D. Chioudhary, R. K. Saunthwal, V. Rustagi, M. Patel, R. S. Tiwari, J. Org. Chem. 78(13) (2013) 6657-6669.

G. Thirunarayanan, K. G. Sekar, International Letters of Chemistry, Physics and Astronomy 10(1) (2013) 18-34.

S. Vijayakumar, R. Arulkumaran, R. Sundararajan, S. P. Sakthinathan, R. Suresh, D. Kamalakkannan, K. Ranganathan, K. Sathiyamoorthy, V. Mala, G. Vanangamudi, G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 9(1) (2013).

M. A. Khalilzadeh, I. Yavari, Z. Hossaini, H. Sadeghifar, Monatsch Chem. 140 (2009) 467-471.

R. Sundararajan, R. Arulkumaran, S. Vijayakumar, D. Kamalakkannan, R. Suresh, S. John Joseph, K. Ranganathan, S. P. Sakthinathan, G. Vanangamudi, G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 1 (2014) 67-73.

K. G. Sekar, G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 8(3) (2013) 249-258.

S. B. Sapkal, K. F. Shelke, A. H. Kategaonkar, M. S. Shingare, Green Chem. Lett. 2(2) (2009) 57-60.

G. Thirunarayanan, K. Ravi, International Letters of Chemistry, Physics and Astronomy 14 (2013) 44-57.

S. P. Sakthinathan, R. Suresh, V. Mala, K. Sathiyamoorthi, D. Kamalakkannan, K. Ranganathan, R. Arulkumaran, S. Vijayakumar, R. Sundararajan, G. Vanangamudi, G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 6 (2013).

Z. Turgut, E. Pelit, A. Koycil, Molecules. 12 (2007) 345-352.

G. Thirunarayanan, P. Mayavel, K. Thirumurthy, Spectrochim. Acta 91A (2012) 18-22.

A. W. Bauer, W. M. M. Kirby, J. C. Sherris, M. Truck, Am. J. Clin. Pathol. 45 (1966) 493-496. (Received 25 November 2013; accepted 29 November 2013).

Show More Hide

Cited By:

[1] S. Alotaibi, "Spectroscopic and Biophysical Studies on Chalcones and Schiff Bases Derived from Chromen-2-one and Quinoline-2(1H)-one Derivatives as Antibacterial Agents", Asian Journal of Chemistry, Vol. 32, p. 1719, 2020

DOI: https://doi.org/10.14233/ajchem.2020.22604