Comparative study of microwave assisted and conventional synthesis of novel 2-quinoxalinone-3- hydrazone derivatives and its spectroscopic properties

International Journal of Physical Sciences

Volumn 4, Issue 4, 2009, Pages 156-164

  Ajani, Olayinka O ^a   Obafemi, Craig A ^b   Ikpo, Chinwe O ^a   Ajanaku, Kolawole O ^a   Ogunniran, Kehinde O ^a   James, Oladele Olusola ^a  

^a Covenant University ^*  (Nigeria)

^b OBAFEMI AWOLOWO UNIVERSITY   (Nigeria)

Author keywords

3 hydrazinoquinoxalin 2(1h) one; Conventional heating; Isatin; Microwave irradiation; Uv visible

Indexed keywords

EID: 70350530713     PISSN: 19921950     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (42)

1. Abd-Elhafez OM, El-khrisy ED, Badria F, Fathy AD (2003). Synthesis and biological Investigations of new thiazolidinone and oxadiazoline coumarin derivatives. Arch. Pharm. Res. 26(9): 686-696.
2. Abdellatif M, Salabeldin M, Alphy K (2008). Studies with enaminonitriles: synthesis and chemical reactivity of 2-phenyl-3-piperidin-1- yl acrylonitrile under microwave heating. J. Heterocycl. Chem. 45: 307-310.
3. Ali MM, Ismail MMF, El-Gaby MSA, Zahran MA, Ammar YA (2000). Synthesis and anti- microbial activities of some novel quinoxalinone derivatives. Molecules 5: 864-873.
4. Badran MM, Abouzid KAM, Hussein MHM (2003). Synthesis certain substituted quinoxalines as anti-microbial agent part ii. Arch. Pharm. Res. 26: 107-113.
5. Bijev A (2006). New heterocyclic hydrazones in the search for antitubercular agents: synthesis and in-vitro evaluations. Lett. Drug Des. Discov. 3: 506-512.
6. Bogdal D, Jaskot K (2000). Synthesis of vinyl monomers with active azaaromatic groups: phase- transfer catalytic approach. Synth. Commun. 38: 3341-3352.
7. Bogdal D, Yashchuck V, Pielichowski J, Ogulchansky T, Warzala M, Kudry V (2002). Synthesis and spectral investigation of alkyl methacrylates with halogenated carbazolyl pendant group for photonic application. J. App. Polym. Sci. 84: 1650-1656.
8. Chang W-J, Yen W-B, Sun C-M (2003). Microwave-assisted soluble polymer-supported synthesis of benzopiperazinones. Synlett: 11: 1688-1692.
9. Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Roussel J (1986). The use of microwave ovens for rapid organic synthesis. Tetrahedron Lett. 27(3): 279 - 282.
10. Giguerre RJ, Bray TL, Duncan SM, Majetich G (1986). Application of commercial microwave oven to organic synthesis. Tetrahedron Lett. 27(41): 4945- 4948.
11. Hayes BL (2004). Recent advances in Microwave-assisted synthesis. Aldrichim. Acta 37(2): 66-76.
12. Jaso A, Zarranz B, Aldana I, Monge A (2003). Synthesis of new 2-acetyl and 2-benzoylquinoxaline 1,4-di-N-oxide derivatives as antimycobacterium tuberculosis agents. Eur. J. Med. Chem. 38: 791- 800.
13. Kim SH, Kim JH (2003). Synthesis and tautomerism of novel quinoxalines (part i). J. Korean Chem. Soc. 47(3): 241-243.
14. Komurcu SG, Rollas S, Uglen M. Gorrod JW (1995). Evaluation of some arylhydrazones of p-amino benzoic acid hydrazide as antimicrobial agents and their in-vitro hepatic microsomal metabolism. Boll. Chim. Farmac. 134: 375-379.
15. Loupy A, Petit A, Bodgal D. Microwaves and Phase-Transfer Catalysis in : Microwave in organic Synthesis, Loupy A. (Ed.), 2nd Edition, Wiley-VCH Verlag, Weinhein, 2006.
16. McLean NJ, Tye H, Whittaker M (2004). Synthesis of cyclic peptides through hydroxyl side- chain anchoring. Tetrahedron Lett. 45: 933.
17. Mehta PD, Sengar NPS, Subrahmanyam EVS, Satyanarayana D (2006). Synthesis and biological activity studies of some Ajani et al. 163 thiazolidinones and azetidinones. Indian J. Pharm. Sci. 68(1): 103- 106.
18. Muscia GC, Carnevale JP, Bollini M, Asís SE (2008). Microwaveassisted Döbner synthesis of 2- phenylquinoline-4-carboxylic acids and their antiparasitic activities. J. Heterocycl. Chem. 45: 611-614.
19. Nasr MNA (2002). Synthesis and antibacterial activity of fused 1,2,4- triazolo[4,3-a]quinoxaline and oxopyrimido[2,1:5,1]-1,2,4-triazolo[4,3- a]quinoxaline derivatives. Arch. Pharm. Med. Chem. 389-394.
20. Obafemi CA, Akinpelu DA (2005). Synthesis and antimicrobial activity of some 2(1H)- quinoxalinone-6-sulfonyl derivatives. Phosphorus, Sulfur, Silicon Relat. Elem. 180: 1795-1807.
21. Olayiwola G, Obafemi CA, Taiwo FO (2007). Synthesis and neuropharmacological activity of some quinoxalinone derivatives. African J. Biotech. 6(6): 777-786.
22. Outirite M, Lebrini M, Lagrenée M, Bentiss F (2008). New one step synthesis of 3,5-disubstituted pyrazoles under microwave irradiation and classical heating. J. Heterocycl. Chem. 45: 503-506.
23. Pathak VN, Gupta R, Varshney B (2008). A one pot synthesis of 2-aryl- 4H-1-benzopyran-4-ones under coupled microwave phase transfer catalysis and ultrasonic irradiation. J. Het. Chem. 45: 589-592.
24. Pielichowski K Bogdal D, Pielichowski J, Boron A (1998). Post-cure effect of long-chain alkylene dimethacrylates. Angew. Makromol. Chemie. 257: 59-62.
25. Qingqing S, Shujiang T, Chunmei L, Longji C, Dianxiang Z, Qian W, Bo J, Yan Z.; Wenjuan H (2008). Green and high efficient synthesis of triaza-benzo[b]fluoren-6-one derivatives in water under microwave irradiation. J. Het. Chem. 45: 411-416.
26. Ragavendran J, Sriram D, Patel S, Reddy I, Bharathwajan N, Stables J, Yogeeswari P (2007). Design and synthesis of anticonvulsants from a combined phthalimid-GABA-aniline and hydrazone pharmacophore. Eur. J. Med. Chem. 42: 146-151.
27. Rashed N, El Massry AM, El Ashry E-SH, Amer A, Zimmer H (1990). A facile synthesis of novel triazoloquinoxalinones and triazinoquinoxalinones. J. Het. Chem. 27: 691-694.
28. Refaat HM, Moneer AA, Khalil OM (2004). Synthesis and anti-microbial activity of certain novel quinoxalines. Arch. Pharm. Res. 27: 1093-1098.
29. Rodrigo DP, Faustino MAF, Pinto DCGA, Neve MGPMS, Cavaleiro JAS (2008). Kinetic study of meso-tetraphenylporphyrin synthesis under microwave irradiation. J. Heterocycl. Chem. 45: 453-460.
30. Rollas S, Küçükgüzel ŞG (2007). Biological activities of hydrazone derivatives. Molecules 12: 1910-1939.
31. Rowan SJ, Cantrill SJ, Cousins GRL, Sanders JKM, Stoddart JF (2002). Dynamic covalent chemistry. Angew. Chem. 114: 938-993.
32. Salgin-Gökşen U, Gökhan-kelekçi N, Göktas , Köysal Y, Kiliç E, Işik Ş, Aktay G, Özalp M (2007). 1-Acylthiosemicarbazides, 1,2,4-triazol- 5(4H)-thiones 1,3,4-thiadiazoles and hydrazones containing 5- methyl-2-benzoxazoline: synthesis, analgesic, anti-inflammatory and antimicrobial activities. Bioorg. Med. Chem. 15: 5738-5751.
33. Sanetra J, Bogdal D, Warzala M, Boron A (2002). Photo- and electroluminescence properties of polymethacrylates with carbazolyl and fluorescent pendant groups. Chem. Mat. 14: 89-95.
34. Sha YW, Wang Y, Ge J, Wang X (2001). The rapid synthesis of Schiffbases without solvent under microwave irradiation. Chin. J. Org. Chem. 21: 102.
35. Sridhar SK, Ramesh A (2001). Synthesis and pharmacological activities of hydrazones, Schiff and mannich bases of isatin derivatives. Biol. Pharm. Bull. 24(10): 1149-1152. (Pubitemid 33049077)
36. Sridharan V, Perumal PT, Avendaño C, Menéndez CJ (2007). The first aza Diel-Alder reaction involving an ,α βunsaturated hydrazone as the dienophile : stereoselective synthesis of C-4 functionalized 1,2,3,4-tetrahydroquinolines containing a quaternary stereocenter. Org. Biomol. Chem. 5: 1351-1353.
37. Su D-S, Bock MG (2005). 2-Quinoxalinone derivatives as bradykinin antagonists and novel compounds. US Patent Appl. (20050020591).
38. Tinh DV, Stadlbauer W (2008). Synthesis of 5-mono and 5,7-diamino pyrido[2,3-d]pyrimidinediones with potential biological activity by regioselective amination. J. Heterocycl. Chem. 45: 821-830.
39. Vanetsev AS, Makshina EV, Oleynikov NN, Tret?yakou YD, Romanovskii BV (2005). Microwave Synthesis of Lanthanum Strontium Cobaltites and Study of Their Catalytic Activity Doklady Akademii Nauk 405(2): 204-207.
40. Vicini P, Zani F, Cozzini P, Doytchinova I (2003). Hydrazones of 1.2- benzisothiazole hydrazide: synthesis, antimicrobial activities and QSAR investigation. Eur. J. Med. Chem. 37(7): 553-564.
41. Wenxiang H, Jianying W (2001). Combinatorial catalysis with physical, chemical and biological methodologies. Chem. Mag. 3(9): 44.
42. Zhenjiang L, Weisi L, Yingjie S, He H, Pingkai O (2008). Facile synthesis of quinoxalinea catalyzed by amidosulfonic acid. J. Heterocycl. Chem. 45: 285-288.