RESEARCH ARTICLE

 

Facile synthesis of 2-(1,3-benzoxazol/benzothiazol-2-yl)-3H-benzo[f]chromen-3-one as blue fluorescent brighteners

 

 

Hosanagara N. Harishkumar; Kittappa M. Mahadevan^*; Jagadeesh N. Masagalli

Department of Post Graduate Studies and Research in Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta-577 451, Karnataka, India

 

 

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ABSTRACT

A novel synthetic method was developed to prepare new fluorescent 2-(1,3-benzoxazol/benzothiazol-2-yl)-3H-benzo [f]chromen-3-one derivatives 3a-p by the Knoevenagel condensation between 2-hydroxy-1-naphthaldehyde and benzothiazole-2-yl-aceatates or N-methyl benzoxazole-2-yl-acetates using choline chloride/urea ionic liquid as a green catalyst. The results of fluorescence studies revealed that all the compounds show moderate to low emission intensities and are expressed in the form of quantum yields.

Keywords: Benzooxazolyl-3H-benzo[f]chromen-3-one, benzothiazolyl-3H-benzo[f]chromen-3-one, choline chloride/urea, fluorescent brighteners

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Full text available only in PDF format.

 

Acknowledgements

We are thankful to the Department of Post Graduate Studies and Research in Chemistry, for providing necessary facilities to carry out the present work, Karnataka University, Dharwad, for fluorescence spectral analysis and the Indian Institute of Science, Bangalore, for providing spectral data.

 

References

1 H.M. Kim, X.Z. Fang, PR. Yang, J.S. Yi, Y.G. Ko, M.J. Piao, Y.D. Chung, Y.W. Park, S.J. Jeon and B.R. Cho, Tetrahedron Lett., 2007, 48, 2791-2795.         [ Links ]

2 X. Li, Y.X. Zhao, T. Wang, M.Q. Shi and F.P. Wu, Dyes Pigments, 2007, 74, 108-112.         [ Links ]

3 S.W. Culligan, A.C.A. Chen, J.U. Wallace, K.P. Klubek, C.W. Tang and S.H. Chen, Adv. Funct. Mater., 2006, 16, 1481-1487.         [ Links ]

4 S.F. Hsu, C.C. Lee, S.W. Hwang, H.H. Chen, C.H. Chen and A.T. Hu, Thin Solid Films, 2005, 478, 271-274.         [ Links ]

5 L.S. Hung and C.H. Chen, Mater. Sci. Eng., 2002, R39, 143-222.         [ Links ]

6 M.S. Kim, J.T. Lim, C.H. Jeong J.H. Lee and G.H. Yeom, Thin Solid Films, 2006, 515, 891-895.         [ Links ]

7 Seong-II Um, Dyes Pigments, 2007, 75, 185-188. And reference cited therein.         [ Links ]

8 S.H. Zhou, J.H. Jia, J.R. Gao, L. Han and W.J. Sheng, Dyes Pigments, 2010, 86, 123-128.         [ Links ]

9 I.I.G. Jones, W.R. Jackson, C. Choi and WR. Bergmark, J. Phys. Chem, 1985, 89, 294-300.         [ Links ]

10 E. Gikas, M. Parissi-Poulou, M. Kazanis and A. Vavagiannis, Anal. Chim. Acta, 2003, 489, 153-163.         [ Links ]

11 (a) L.G. Lee, G.M. Berry and C.H. Chen, Cytometry, 1989, 10, 151-164.         [ Links ] (b) J.E. Whitaker, R.P. Haugland and F.G. Prendergast, Anal. Biochem, 1991, 194, 330-344.         [ Links ] (c) W.M.M. Fabian, S. Schuppler and O.S. Wolfbeis, J. Chem. Soc. Perkin Trans., 1996, 853-856.         [ Links ]

12 H. Ammar, S. Fery-Forgues and R. El Gharbi, Dyes Pigments, 2003, 57, 259-265.         [ Links ]

13 S. Sastry, Biophys. Chem, 2001, 91, 191-208.         [ Links ]

14 M. Chiyomi, M. Toshinobu, K. Yasuko, T. Kenichiro, Y. Hideyuki, N. Hitoshi, Y. Masatoshi and T. Akira, Chem. Pharm. Bull., 2005, 53, 750-758. And references cited therein.         [ Links ]

15 G. Rajesha. N.H.S. Bhojya, H.N. Harishkumar, K.M. Hosamani and K.M. Mahadevan, Arkivoc., 2009, (ii), 11-19. And references cited therein.         [ Links ]

16 G. Rajesha, H.C. Kiran Kumar, H.S. Bhojya Naik and K.M. Mahadevan, S. Afr. J. Chem., 2011, 64, 88-94.         [ Links ]

17 Rajesha, H.C. Kiran Kumar, H.S.B. Naik and K.M. Mahadevan, Org. Chem.: Indian J., 2011, 7.         [ Links ]

18 K. Mazaahir and K. Parven, J. Chem. Research (S), 1997, 178-179.         [ Links ]

19 Z. Anlian, J. Tao, H. Buxing, Z. Jicheng, X. Ye and M. Xiumin, Green Chem., 2007, 9, 169-172. And references cited therein.         [ Links ]

20 (a) A. Mols, R.J. Vendra and T.K. Axel, J. Endo Chem: Phys. Dut. Aspects, 2005, 125.         [ Links ] (b) A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed and V. Tambyrajah, Chem Commun., 2003, 11, 70-77.         [ Links ]

21 V. Hassan and V. Sevil, Synth. Commun., 2009, 39, 1666-1678. And references cited therein.         [ Links ]

22 A. Srinivasa, K.M. Mahadevan, K.T.H. Suresh and H. Vijaykumar, Monatsh. Chem, 2008, 139, 1475-1478.         [ Links ]

23 A. Sudhakara, H. Jayadevappa, H.N. Harishkumar and K.M. Mahadevan, Lett. Org. Chem, 2009, 6, 159-164.         [ Links ]

24 G.K. Nagaraja, G.K. Prakash, M.N. Kumaraswamy, V.P. Vaidya and K.M. Mahadevan, Arkivoc., 2006, XV, 160-168.         [ Links ]

25 P.V. Putta, B.S.Sherigara, K.M. Mahadevan and H. Vijaykumar, Synth. Commun, 2010, 40, 2220-2231.         [ Links ]

26 A.G. Mahesh, H. Jayadevappa, A. Sudhakara and K.M. Mahadevan, Lett. Org. Chem, 2008, 5, 628-632.         [ Links ]

27 P.V. Putta, A. Srinivasa and K.M. Mahadevan, Synth. Commun., 2011, 41, 2186-2194.         [ Links ]

28 H.N. Harishkumar, H. Vijaykumar and K.M. Mahadevan, Synth. Commun., 2010. 40, 3281-3289.         [ Links ]

29 H.N. Harishkumar, K.M. Mahadevan, H.C. Kiran Kumar and N.D. Satyanarayan, Org. Commun., 2011, 4, 26-32.         [ Links ]

30 C.S. Hong, D. Fa-Xiang and L.C. Steven, Org. Lett., 2006, 8, 1447-1450.         [ Links ]

31 A. Alessandro, B. Silvia, F. Antonio and A.P. Giorgio, J. Org. Chem., 2002, 67, 5753-5772.         [ Links ]

32 S.N. Kovalenko, M.V. Vasil'ev, I.V. Sorokina, V.P. Chernykh, A.V Turov and S.A. Rudnev, Chem Heterocycl Compd., 1998, 34(12), 1412-1415.         [ Links ]

33 G. Signore, R. Nifosi, L. Albertazzi, B. Storti and R. Bizzarri, J. Am. Chem. Soc., 2010, 132, 1276-1288.         [ Links ]

34 K.V Joseph and VV Somayanjulu, J. Indian Chem. Soc., 1979, 56, 505-507.         [ Links ]

35 P. Moeckli, Dyes Pigments, 1980, 1, 3-15.         [ Links ]

36 L. Han, S.J. Jia, W. Sheng, Y. Li and J. Gao. Heterocycl Commun., 2009, 15, 245-250.         [ Links ]

37 V. Dryanska, Synth. Commun, 1987, 17, 203-209.         [ Links ]

38 A. Dorit, P.B. Arthur, G.Y. David, S.P. Andrew, W.P. Bradley, S. Bailin and V. Jyothi, PCT Int. Appl, 2002, 106.         [ Links ]

 

 

Received 22 July 2011
Revised 10 October 2011
Accepted 8 December 2011

 

 

* To whom correspondence should be addressed. E-mail: mahadevan.kmm@gmail.com