K2CO3: A Mild and Efficient Catalyst for the Synthesis of Pyran Annulated Heterocyclic Systems by Grinding Method Under Solvent-Free Conditions

Open access

Abstract

The potassium carbonate was applied as a green and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic systems, via the condensation between aromatic aldehydes, malononitrile and dimedone/1-naphtole by a grinding method at room temperature and solvent-free conditions. Short reaction times, environmentally friendly procedure and excellent yields are the main advantages of this procedure which makes it more economic than other environmentally synthetic methods.

1. Sheldon, R.A. Selective catalytic synthesis of fine chemicals: opportunities and trends J. Mol. Catal. 1996, 107, 75-83.

2. Tanaka, K.; Toda, F. Solvent-Free Organic Synthesis. Chem. Rev. 2000, 100, 1025-1074.

3. Wu, J.Y.; Fong, W.F.; Zhang, J.X.; Leung, C.H.; Kwong, H.L.; Yang, M. S.; Li, D; Cheung, H.Y. Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix Peucedani. Eur. J. Pharmacol. 2003, 473, 9-17.

4. Raj, T.; Bhatia, R.K.; Sharma, M.; Saxena, A.K.; Ishar, M.P. Cytotoxic activity of 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4H-chromene-3-carbothioic acid N-phenylamides. Eur. J. Med. Chem. 2010, 45, 790-794.

5. Rueping, M.; Sugiono, E.; Merino, E. Asymmetric Organocatalysis: An Efficient Enantioselective Access to Benzopyranes and Chromenes. Chem. A. Eur. J. 2008, 14, 6329-6332.

6. Morgan, L.R.; Jursic, B.S.; Hooper, C.L.; Neumann, D.M.; Thangaraj, K.; LeBlanc, B. Anticancer activity for 4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) analogues and Their abilities to interact with lymphoendothelial cell surface markers. Bioorg. Med. Chem. Lett. 2002, 12, 3407-3411.

7. Moon, D.O.; Kim, K.C.; Jin, C.Y.; Han, M.H.; Park, C.; Lee, K.J.; Park, Y.M.; Choi, Y.H.; Kim, G.Y. Inhibitory effects of eicosapentaenoic acid on lipopolysaccharide-induced activation in BV2 microglia. Int. Immunopharmacol. 2007, 7, 222-229.

8. Kumar, A.; Maurya, R.A.; Sharma, S.; Ahmad, P.; Singh, A.B.; Bhatia, G.; Srivastava, A.K. Pyranocoumarins: A new class of antihyperglycemic and anti-dyslipidemic agents. Bioorg. Med. Chem. Lett. 2009, 19, 6447-6451.

9. Konkoy, C.S., Fick, D.B., Cai, S.X., Lan, N.C. Keana, J.F.W. (2001). PCT Appl. WO 0075123; Chem. Abstr. (2000), 134, 29313a.

10. Hanna L. Calanolide A: a natural non-nucleoside reverse transcriptase inhibitor. BETA: bulletin of experimental treatments for AIDS: a publication of the San Francisco AIDS Foundation. 12, 8. (1999).

11. Flavin, M.T.; Rizzo, J.D.; Khilevich, A.; Kucherenko, A.; Sheinkman, A.K.; Vilaychack, V.; Lin, L.; Chen, W.; Greenwood, E.M.; Pengsuparp, T.; Pezzuto, J.M. Synthesis, Chromatographic Resolution, and Anti-Human Immunodeficiency Virus Activity of (±)-Calanolide A and Its Enantiomers. J. Med. Chem. 1996, 39, 1303-1313.

12. De Andrade-Neto, V.F.; Goulart, M.O.; MJ Da silva, MDCFR Pinto, AV Pinto, MG Zalis, LH Carvalho and AU Krettli. Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo. Bioorg. Med. Chem. Lett. 2004, 14, 1145-1149.

13. Agarwal, A.; Srivastava, K.; Puri, S.K.; Chauhan, P.M.S. Synthesis of 4-pyrido-6-aryl-2-substituted amino pyrimidines as a new class of antimalarial agents. Bioorg. Med. Chem. 2005, 13, 6226-6232.

14. Shaabani, A.; Ghadari, R.; Sarvary, A.; Rezayan, A.H. Synthesis of Highly Functionalized Bis(4H-chromene) and 4H-Benzo[g]chromene Derivatives via an Isocyanide-Based Pseudo-Five-Component Reaction. J. Org. Chem. 2009, 74, 4372-4374.

15. Elinson, M.N.; Dorofeev, A.S.; Miloserdov, F.M.; Ilovaisky, A.I.; Feducovich, S.K.; Belyakov, P.A.; Nikishin, G.I. Catalysis of Salicylaldehydes and Two Different C—H Acids with Electricity: First Example of an Efficient Multicomponent Approach to the Design of Functionalized Medicinally Privileged 2-Amino-4H-Chromene Scaffold. Adv. Synth. Catal. 2008, 350, 591-601.

16. Hafez, E.A.A.; Elnagdi, M.H.; Elagamey, A.G.A.; El-taweel, F.M.A.A. Nitriles in Heterocyclic Synthesis: Novel Synthesis of Benzo[c]coumarin and of Benzo[c]pyrano[3,2-c]quinoline Derivatives. Heterocycles, 1987, 26, 903-907.

17. Esmaeilpour, M.; Javidi, J.; Dehghani, F.; Dodeji, F.N. A green one-pot three-component synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives using a Fe3O4@SiO2–imid–PMAn magnetic nanocatalyst under ultrasonic irradiation or reflux conditions. RSC Adv. 2015, 5, 26625-26633.

18. Shirini, F.; Abedini, M.; Zarrabzadeh, S.; Seddighi, M. Efficient synthesis of 4H-pyran derivatives using a polymeric catalyst based on PVP. J. Iran. Chem. Soc. 2015, 12, 2105-2113.

19. Nemouchi, S.; Boulcina, R.; Carboni, B.; Debache, A. Phenylboronic acid as an efficient and convenient catalyst for a three-component synthesis of tetrahydrobenzo[b]pyrans. C. R. Chimie. 2012, 15, 394-397.

20. Yang, J.; Liu, S.; Hu, H.; Ren, S.; Ying, A. One-pot three-component synthesis of tetrahydrobenzo[b]pyrans catalyzed by cost-effective ionic liquid in aqueous medium. Chin. J. Chem. Eng. 2015, 23, 1416-1420.

21. Mohammadi AA, Asghariganjeh MR, Hadadzahmatkesh A. Synthesis of tetrahydrobenzo[b]pyran under catalysis of NH4Al(SO4)2·12H2O (Alum). Arab. J.Chem., 2017, 10, S2213-S2216.

22. Khaksar, S.; Rouhollahpour, A.; Talesh, S.M. A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium. J. Fluor. Chem. 2012, 141, 11-15.

23. Jin, T.S.; Xiao, J.C.; Wang, S.J.; Li, T.S. Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media. Ultrason. Sonochem. 2004, 11, 393-397.

24. Santra, S.; Rahman, M.; Roy, A.; Majee, A.; Hajra, A. Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyrans. Org. Chem. Int., 2014, ID 851924, 1-8.

25. Balalaie, S.; Bararjanian, M.; Amani, A.M.; Movassagh, B. (S)-Proline as a Neutral and Efficient Catalyst for the One-Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media. Synlett, 2006, 263-266.

26. Essamlali, Y.; Amadine, O.; Maati, H.; Abdelouahdi, K.; Fihri, A.; Zahouily, M.; Varma, R.S.; Solhy, A. Highly Efficient One-Pot Three-Component Synthesis of Naphthopyran Derivatives in Water Catalyzed by Phosphates. ACS Sustainable Chem. Eng., 2013, 1, 1154-1159.

27. Kangani, M.; Hazeri, N.; Maghsoodlou, M.T. A Mild and Environmentally Benign Synthesis of Tetrahydrobenzo[b]pyrans and Pyrano[c]chromenes Using Pectin as a Green and Biodegradable Catalyst. J. Chin. Chem. Soc, 2016, 63, 896-901.

28. Hazeri, N.; Maghsoodlou, M.T.; Mir, F.; Kangani, M.; Saravani, H.; Molashahi, E. An efficient one-pot three-component synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives using starch solution as catalyst. Chin. J. Catal. 2014, 35, 391-395.

29. Noori Sadeh, F.; Maghsoodlou, M.T.; Hazeri, N.; Kangani, M. A facile and efficient synthesis of tetrahydrobenzo[b]pyrans using lactose as a green catalyst. Res. Chem. Intermed. 2015, 41, 5907-5914.

30. Maghsoodlou, M. T.; Masoumnia, A.; Mousavi, M. R.; Hazeri, N.; Aboonajmi, J.; Habibi-Khorasani, S. M.; Kiaee, S. A green protocol for synthesis of pyran annulated heterocyclic systems using Na2SO4 as an efficient catalyst. Iran. J. Catal. 2015, 2, 169-174.

31. Maghsoodlou, M.T.; Safarzaei, M.; Mousavi, M.R.; Hazeri, N.; Aboonajmi, J.; Shirzaei, M. A green and novel three-component one-pot synthesis of tetrahydrobenzopyran, pyrano[2,3-d]pyrimidine, and 3,4-dihydropyrano[c]chromene derivatives using sodium acetate. Iran J. Org. Chem. 2014, 6, 1197-1202.

32. Bodaghifard, M.A.; Ahadi, N. One pot synthesis of tetrahyrobenzo[b]pyran and dihydropyrano[c]chromene derivatives using ammonium Alum in green media. Bulg. Chem, Commun. 2015, 47, 603-606.

33. Kiasat, A.R.; Hamid, S.; Saghanezhad, S.J. Synthesis and Characterization of a Novel Nanosilica Supported Bipyridinium Chloride Nanocomposite and its Application as a Basic Catalyst in the One-pot Preparation of Tetrahydrobenzo[b]pyran, Dihydropyrano[3,2-c]chromene and Dihydropyrano[4,3-b]pyran Derivatives. Nanochem Res., 2016, 1, 157-165.

34. Zolfigol, M.A.; Bahrami-Nejad, N.; Afsharnadery, F.; Baghery, S. 1-Methylimidazolium tricyanomethanide {[HMIM]C(CN)3} as a nano structure and reusable molten salt catalyst for the synthesis of tetrahydrobenzo[b]pyrans via tandem Knoevenagel-Michael cyclocondensation and 3,4-dihydropyrano[c]chromene derivatives. J. Mol. Liq., 2016, 221, 851-859.

35. Baghernejad, B.; Heravi, M.M.; Oskooie, H.A. A Novel and Efficient Catalyst to One-Pot Synthesis of 2-Amino-4H-chromenes by p-Toluenesulfonic Acid. J. Korean Chem. Soc., 2009, 53, 631-634.

Acta Chemica Iasi

The Journal of "Alexandru Ioan Cuza" University from Iasi

Journal Information

Metrics

All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 165 165 21
PDF Downloads 63 63 14