Rapid Ecofriendly Synthesis of Benzocoumarins by Microwave Irradiation and Their Antimicrobial Screening

Gunjan Shrivastava; Vikas Shrivastava; D.S. Seth

Gunjan Shrivastava Dept. of Chemistry, St. John’s College, Agra, Uttar Pradesh
Vikas Shrivastava Dept. of Biotechnology, Arni University, Kangra, Himachal Pradesh.
D.S. Seth Dept. of Chemistry, St. John’s College, Agra, Uttar Pradesh

Abstract

Benzo-annulated coumarin derivatives show wide application in organic light-emitting devices and are used as electron transporting emitters. In addition, coumarin family is an important building block for the synthesis of a variety of fascinating polycyclic unnatural products. 5-6Benzocoumarin derivatives show antimicrobial, antiinflammatory and anticancer activities. The utility of microwaves in heterocyclic synthesis is now receiving considerable attention. As a part of our study, aiming to explore potential utility of microwaves as an energy source for heterocyclic synthesis, it has been reported that synthesis of benzocoumarins of potential interest as pharmaceuticals and/or photochromic dyes and investigation of the possibility of conducting these reactions under microwave irradiation in addition to the standard thermal conditions has taken place. The compounds are synthesized by conventional and microwave method. Malonamic acid of 4-Chloro-2,5-dimethoxy aniline was treated with 2-hydroxy-1-naphthaldehyde. The synthesis by microwave provides better yield, more pure compounds and cleaner synthesis route. This study explains the synthesis and wide range of pharmaceutical properties of new substituted benzocoumarins.

Keywords: Benzocoumarins, schiff bases, microwave irradiation, antimicrobial activities.

References

1. (a) Harayama T, Yasuda H. Antitumor activity, Heterocycles 1997; 46: 61. (b) Pauli RM. Anticoagulants In Handb. Exp. Pharmacol.1997;191. (c) Wang S, Milne GWA, Yan X, Posey IJ, Nicklaus MC, Graham L, Rice WG. HIV-1 protease inhibitors. J. Med. Chem. 1996; 39: 2047.
2. Guarneri M. Bull. Chem. Form. 1990; 99:259.
3. Albert O, Bergonzio G. Farmaco (Pavia) Ed. Sci. 1961; 16: 557.
4. Wierzxhowsk KL, Lifonskao E, Surger D. J. Am. Chem. Soc.1965; 87.
5. Gerg GH, Prakash C. J. Med. Chem. 1971; 4: 175.
6. Hammad A, El-Sayed AS, Islam IE, Shafik N. J. Chem.Soc. Pax. 1990; 12: 292 (Chem. Abstr. 1990; 115: 71279s).
7. Kulkarni GM, Kulkarni HV, Patil HV, Shridhar DB, Laxmana M. Rev. Roum. Chim. 1990; 35: 549.
8. Harvey RG, Cortex C, Ananthanarayan TP, Schmolka S. S. J. Org. Chem. 1988; 53: 3936.
9. Buu-Hoi NP, Lavit D. J. Chem. Soc., 1956; 1743-1748.
10. Pardanani JH, Sethna S. J. Indian Chem. Soc. 1978; 55: 806-809.
11. Caddick S. Tetrahedron. 1995; 51:10403.
12. Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jacqnault P, Mathe D. Synthesis. 1998;1213.
13. Perreux L, Loupy A. Tetrahedron. 2001; 57: 9199.
14. Lidstrom P, Tierney J, Wathey B, Westman J. Tetrahedron. 2001; 57: 9225.
15. Al-Zaydi KM. J. Saudi Chem. Society, 2002; 477.
16. Al-Zaydi KM, Hafez EA, Elnagdi MH. J. Chem. Res. 2000 (S); 4(M) : 510.
17. Al-Naggar AA, Abdel-Khalik MM, Elnagdi MH. J. Chem. Res. 1999(S); 648 (M) : 2801.