A Detailed Bromination Study of 7-Hydroxy-4-Methyl Benzopyran-2-One Under Classical Method and Microwave Irradiation

Authors

  • Vijay D. Gangan  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Ajaykumar C. Singh  Department of Chemistry, R. D. National College, Bandra (West) Mumbai, Maharashtra, India
  • Ruchira Joshi  Department of Chemistry, R. D. National College, Bandra (West) Mumbai, Maharashtra, India
  • Amod V. Tamhankar  COO, N. S. Chemicals, 601, Devavrata, sector 17, Vashi Navi Mumbai Maharashtra, India
  • Kalpana J. Bhatwadekar  Technical Director, Sirmaxo Chemicals Private Limited, Plot No.:, E, 35, Palghar, Tarapur Road, Tarapur M.I.D.C., Boisar, Maharashtra, India
  • Shyamlal T. Yadav  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Suyog S. Daye  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Dattatraya A. Dute  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Sakharam K. Godage  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Manoj Yewale  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Gaurav Pimple  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India
  • Arjun L. Ghorpade  Department of Chemistry, Loba Chemie Pvt. Ltd.,. Plot No. D-22, M.I.D.C.. Tarapur, Boisar Palghar, Maharashtra, India

DOI:

https://doi.org//10.32628/IJSRST1196231

Keywords:

Substituted Benzopyran, Classical Method, Microwave Irradiation, Protic and Aprotic Solvents, Allylic and Vinylic Bromination, 1H NMR, TOF MS ES and Elemental Analysis.

Abstract

7-Hydroxy-4-methyl benzopyran-2-one, Benzopyran a class of coumarin derivative, has been subjected for bromination under classical method, microwave irradiation and solvent-free protocol for allylic and vinylic bromination using liquid Br2, organic bromides, NBS, HBr-H2O2 and DDH as brominating agent under different protic and aprotic solvents. The efficacy of the bromination of benzopyran under classical method and microwave irradiation has been established. The effects of the bromination and location of the substituents on the outcome of the reaction have been rationalized by using 1H NMR and IR spectrum. Few of them showing promising antibacterial activity.

References

  1. Kumar, S., saini, A., Sandhu, J. S. (2007). LiBr-Mediated, solvent free von Pechmann reaction : facile and efficient method for the synthesis of 2H-chromen-2-ones. ARKIVOC, XV, pp. 18 - 23.
  2. Lin, C. M., Huang, S. T., Lee, F. W., Sawkuo, H., Lin, M. H. (2006). 6-Acyl-4-aryl /alkyl-5,7-dihydroxycoumarins as anti-inflammatory agents. Bioorganic & Medicinal Chemistry, 14 (13), pp. 4402 - 4409.
  3. Bhat, M. A., Siddiqui, N., Khan, S. A. (2006). Synthesis of novel thioureido derivatives of sulfonamides and thiosemicarbazido derivatives of coumarin as potential anticonvulsant and analgesic agents. Indian J. Pharm. Sci., 68 (1), pp. 120 - 123.
  4. Massimo,C., Francesco, E., Federica, M., Carla, M. M., Prieto, G. S., Carlos, R. J. (2003).
  5. Synthesis of Collinin, an antiviral coumarin. Aust. J. Chem., 2003, 56 (1), pp. 59 - 60.
  6. Ruszat, R., Wyler, S., Forster, T., Reich, O., Christian, G. S., Thomas, C. G., Sulser, T. and Bachmann, A. (2007). Safety and effectiveness of photoselective vaporization of the prostate (PVP) in patients on ongoing oral anticoagulation. Eur. Urol., 51, pp. 1031 -10 41.
  7. Tyagi, A. K, Raj, H. G, Vohra, P., Gupta, G., Kumari, R., Kumar, P., Gupta, R. K. (2003). Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. Eur J.Med. Chem, 40 (4), pp. 413 - 420.
  8. Modranka, J. N., Nawrot, E., Graczyk, J. (2006). In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem., 41 (11), pp. 1301 - 1309.
  9. Sardari, S., Mori, Y., Horita, K., Micetich, R.G., Nishibe, S., Daneshtalab, M. (1999). Synthesis and antifungal activity of coumarins and angular furanocoumarins. Bioorg. Med.Chem., 7, pp. 1933 - 1940.
  10. a) Huang, Li., Yuan, X., Yu, D., Lee, K. H., Chen, C. H. (2005). Mechanism of action and resistant profile of anti-HIV-1 coumarin derivatives. Virology, 332 (2), pp. 623 - 628. b) Hussien, F. A., Keshe, M., Alzobar, K., Merza, J., Karam, A. (2016). Synthesis and Nitration of 7-Hydroxy-4-Methyl Coumarin via Pechmann Condensation Using Eco-Friendly Medias International letters of Chemistry, Physics and Astronomy, 69, pp. 66 - 73.
  11. Elinos-Baez, C. M., Leon, ,F., Santos, E. (2005). Effects of coumarin and 7-OH-coumarin on bcl-2 and Bax expression in two human lung cancer cell lines in vitro. Cell. Biol. Int., 29, pp. 703 - 708.
  12. Mohanty, N., Rath, P. C., Rout, M. K.. (1967). J. Indian Chem. Soc., 44, pp. 1001 - 1004.
  13. Kennedy, R. O. and Tharnes, R. D. (1997). Coumarins : Biology, Application and Mode of Action,Wiley & Sons, Chichester.
  14. Murray, R. D. H.; Mendez, J.; Brown (1982). The Natural Coumarins: Occurrence, Chemistry and Biochemistry, Wiley and Sons, New York S. A.
  15. Singh, A. C, Joshi, R. N., Pujari, J. S., Satpute, S. M., Gangan V. D., Dubey, R. S., Chakraborty, C. T. (2017). Green synthesis : Bromination study of 7-Hydroxy-4-methylcoumarin with Na-Y type Zeolite without toxic solvents. Journal of Science & Technology - BIONANO FRONTIER, Vol 10 (1), pp. 1 - 4, January - June 2017.
  16. a)Mwambete K. D. and Lyombe F. (2011). Antimicrobial activity of medicated soaps commonly used by Dar es Salaam residents in Tanzania. Indian J. Pharm. Sci., 73 (1) : 92 - 98. b ) Al lafi T. and Ababneh H. (1995). The effect of miswak used in Jordan and Middle East on oral bacteria. International Dental Journal, 45 (3), pp. 218 - 222.

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Published

2019-04-30

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Research Articles

How to Cite

[1]
Vijay D. Gangan, Ajaykumar C. Singh, Ruchira Joshi, Amod V. Tamhankar, Kalpana J. Bhatwadekar, Shyamlal T. Yadav, Suyog S. Daye, Dattatraya A. Dute, Sakharam K. Godage, Manoj Yewale, Gaurav Pimple, Arjun L. Ghorpade, " A Detailed Bromination Study of 7-Hydroxy-4-Methyl Benzopyran-2-One Under Classical Method and Microwave Irradiation, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 6, Issue 2, pp.205-213, March-April-2019. Available at doi : https://doi.org/10.32628/IJSRST1196231