Maher CHERIF, Mariem DEBBABI, Sarra CHORTANI, Anis ROMDHANE, Hichem BEN JANNET

Design and synthesis of new naphtho[2,1-b]pyrano [2,3-d]pyrimidinones under classical and microwave conditions

: A fast and efficient method for the synthesis of naphthopyranopyrimidinones derivatives in excellent yieldswas developed through cyclocondensation reaction between previously prepared pyrimidinic hydrazides and some electrophilic species such as 2,4-pentanedione, 2,5-hexanedione, cyclic anhydrides, and phenylthioisocyanate under microwaveirradiation. Compared to the conventional methods applied, it was found that better yields and shorter reaction timeswere achieved using microwave-assisted synthesis. Structures of all synthesized compounds were established on the basisof spectroscopic methods including 1 H NMR, 13 C NMR, and HRMS-ES.

PDF

___

1. Ambareen, S., Jyotsna, S. M. Cur. Bioact. Comp. 2018, 14, 134-141.
2. Figueiredo, J.; Serrano, J. L.; Cavalheiro, E.; Keurulainen, L.; Yli-Kauhaluoma, J.; Moreira, V. M.; Ferreira, S.; Domingues, F. C.; Silvestre, S.; Almeida, P. Eur. J. Med. Chem. 2018, 143, 829-842.
3. Zhang, W.; Holyoke, C. W. Jr.; Barry, J.; Leighty, R. M.; Cordova, D.; Vincent, D. R.; Hughes, K. A.; Tong, M. T.; McCann, S. F.; Xu, M. et al. Bioorg. Med. Chem. Lett. 2016, 26, 5444-5449.
4. Ikhlass, A.; Sobhi, G.; Mohamed, E.; Mahmoud, E.; Bazada, M. Turk. J. Chem. 2015, 39, 510-531.
5. Nilam, C. D.; Prasad, G. M.; Dattaprasad, M. P. Med. Chem. Res. 2018, 27, 224-234.
6. Oluwole, S. A.; Kaalin, G.; Pramod, K.; Moganavelli, S.; Chunderika, M.; Paravesh, S.; Neil, A. K. Anti-Cancer Agents Med. Chem. 2017, 17, 719-725.
7. Reshma, P.; Digambhar, K.; Priyanka, M.; Sunetra, J.; Ajinkya, P.; Madhukar, D. Chem. Sci. Rev. Lett. 2015, 16, 979-984.
8. Idhayadhulla, A.; Kumar, R. S.; Abdul Nasser, A. J.; Manilal, A. Der Pharma Chemica 2011, 3, 210-218.
9. Joseph, M.; Muchowski, S. H.; Unger, T.; Ackrell, J.; Cheung, P.; Gary, F.; Cook, C. J. J. Med. Chem. 1985, 28, 1033-1037.
10. Dannhardt, G.; Kiefer, W.; Kramer, G.; Maehrlein, S.; Nowe, U.; Fiebich, B. Eur. J. Med. Chem. 2000, 35, 499-510.
11. Ando, Y.; Fuse, E.; Figg, W. D. Clin Cancer Res. 2002, 8, 1964-1973.
12. Freiberg, C.; Fischer, H. P.; Brunner, N. A.; Antimicrob. Agents Chemother. 2005, 49, 749-759.
13. Gokhan-Kelekci, N.; Yabanoglu, S.; Kupeli, E.; Salgin, U.; Ozgen, O.; Ucar, G.; Yesilada, E.; Kendi, E.; Yesilada, A.; Bilgin, A. A.. J. Bioorg. Med. Chem. 2007, 5, 5775-5786.
14. Lin, R.; Chiu, G.; Yu, Y.; Connolly, P. J.; Li, S.; Lu, Y.; Adams, M.; Fuentes-Pesquera, A. R.; Emanuel, S. L.; Greenberger, L. M. Bioorg. Med. Chem. Lett. 2007, 17, 4557-4561.
15. Rajendra, K. W. J. Chem. Pharm. Res. 2011, 3, 136-144.
16. Meghasham, N. N. J. Chem. Pharm. Res. 2011, 3, 38-47.
17. Zafer, A. K. Molecules 2011, 16, 7662-7671.
18. Aboraia, A. S.; Abdel-Rahman, H. M.; Mahfouz, N. M.; El-Gehdy, M. A. Bioorg. Med. Chem. 2006, 14, 1236-1246.
19. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223.
20. Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279-282.
21. Giguere, R. J.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett. 1986, 27, 4945-4948.
22. Lidström, P.; Tierney, J.; Wathey, J.; Westman J. Tetrahedron 2001, 57, 9225-9283.
23. Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2006, 47, 5171-5172.
24. Ameur, R.; Anis, R.; Abderrahim, B. S., Kaouther, M.; Hichem, B. J. Turk. J. Chem. 2014, 38, 210-221.
25. Imen, Z.; Belsem T.; Anis, R.; David, T.; Hichem, B. J. Mediterr. J. Chem. 2011, 1, 145-153.
26. Rahmouni, A.; Romdhane, A.; Besbes, M.; Elie, N.; Touboul, D.; Ben Jannet, H. Mediterr. J. Chem. 2014, 2, 679-690.
27. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
28. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844-14845.
29. Li, J. H.; Wang, D. P.; Xie, Y. X. Tetrahedron Lett. 2005, 46, 4941-4944.
30. Hima, R. K.; Prodeep, P. Cat. Comm. 2007, 8, 179-182.
31. Romdhane, A.; Martin, M. T.; Ben Said, A.; Jabrane, A.; Ben Jannet, H. J. J. Soc. Chim. Tunisie 2012, 14, 127-135.
32. Tozkoparan, B.; Gökhan, N.; Aktay, G.; Yeşilada, E.; Ertan, M. Eur. J. Med. Chem. 2000, 35, 743-750.
33. Demirbas, N.; Ugurluoglu, R.; Demirbas, A. Bioorg. Med. Chem. 2002, 10, 3717-3723.
34. Shivarama Holla, B.; Akberali, P. M.; Shivananda, M. K. Farmaco 2001, 56, 919-927.
35. Mohammed, F. K.; Soliman, A. Y.; Ssawy, A.; Badre, M. G. J. Chem. Pharm. Res. 2009, 1, 213-222.
36. Dinesh, R. P.; Subhash, P. E-Journal of Chemistry 2009, 6, S91-S96.