Comparison of microwave-assisted and conventional preparations of cyclic imides

Tetrahedron Letters

Volumn 51, Issue 17, 2010, Pages 2215-2217

  Upadhyay, Sunil K ^a   Pingali, Subramanya R K ^a   Jursic, Branko S ^a,b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b Stepharm   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE;

ARTICLE; CHEMICAL STRUCTURE; MICROWAVE RADIATION; QUANTITATIVE ANALYSIS; SYNTHESIS;

EID: 77949567795     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.092     Document Type: Article

References (50)

1. Reddy P.Y., Kondo S., Toru T., and Uedo Y.J. Org. Chem. 62 (1997) 2652-2654
2. Walker M.A. J. Org. Chem. 60 (1995) 5352-5355 Tetrahedron Lett. 1994, 35, 665-668
3. Braish T.F., and Fox D.E. Synlett (1992) 979-980
4. Dorta R.L., Francisco C.G., and Suarez E. Tetrahedron Lett. 35 (1991) 1083-1086
5. Nielsen O., and Buchardt O. Synthesis (1991) 819-821
6. Schwartz A.L., and Lerner L.M. J. Org. Chem. 39 (1974) 21-23
7. Mehta N.B., Phillips A.P., Lui F.F., and Brooks R.E. J. Org. Chem. 25 (1960) 1012-1015
8. For recent review on microwave assisted reactions see:. Polshettiwar V., and Varma R.S. Acc. Chem. Res. 41 (2008) 629-639
9. Cappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
10. Shipe W.D., Yang F., Zhao Z., Wolkenberg S.E., Nolt M.B., and Lindsley C.W. Heterocycles 70 (2006) 655-689
11. Polshettiwar V., and Varma R.S. Chem. Soc. Rev. 37 (2008) 1546-1557
12. Man A.K., and Shahidan R. Pure Appl. Chem. 44 (2007) 651-657
13. Mavandadi F., and Pilotti A. Drug Discovery Today 11 (2006) 165-174
14. Razzaq T., Kremsner J.M., and Kappe C.O. J. Org. Chem. 73 (2008) 6321-6329
15. De La Hoz A., Diaz-Ortiz A., and Moreno A. Chem. Soc. Rev. 34 (2005) 164-178
16. Perreux L., and Loupy A. Tetrahedron 57 (2001) 9199-9223
17. Bowman M.D., Schmink J.R., McGowan C.M., Kormos C.M., and Leadbeater N.E. Org. Process Res. Dev. 12 (2008) 1078-1088
18. The laboratory version of our microwave has a cavity size of 21.6 cm in height, 17.30 cm wide, and 25.4 cm deep with two 2.54 cm hole on the top of the microwave for the condenser and thermometer. The magnetron (700 W) was directly wired to variable electronic autotransformer for the control of the magnetron power. ECM meter (10 A) was wired to the magnetron transformer to control the microwave power. The magnetic stirrer was installed beneath the cavity for stirring the reaction mixture. The reaction temperature was measured directly with a thermometer inserted into the reaction mixture through a condenser and/or by infrared reading.
19. For application of ionic liquid see:. Tanaka K. Solvent-free Organic Synthesis (2003), Wiley, VCH, New York
20. Polshettiwar V., and Varma R.S. Pure Appl. Chem. 80 (2008) 777-790
21. Polshettiwar V., and Varma R.S. Curr. Opin. Drug Disc. Dev. 10 (2007) 723-737
22. Strauss C.R., and Varma R.S. Top. Curr. Chem. 266 (2006) 199-231
23. Filho V.C., de Campos F., Correa R., Yunes R.A., and Nunes R.J. Quim. Nova 26 (2003) 230-241
24. Benjamin E., and Hijji Y. Molecules 13 (2008) 157-169
25. Abdel-Aziz A.A.-M. Eur. J. Med. Chem. 42 (2007) 614-626
26. Chernick E.T., Ahrens M.J., Scheidt K.A., and Wasielewski M.R. J. Org. Chem. 70 (2005) 1486-1489
27. Guthrie B., Wang Z., and Li J. Mater. Res. Soc. Symp. Proc. (2008) 1091
28. Santos J.L., Lima L.M., and Chung M.C. Revista de Ciencias Farmaceuticas Basica e Aplicada 27 (2006) 163-167
29. Osby J.O., Martin M.G., and Ganem B. Tetrahedron Lett. 25 (1984) 2093
30. Wuts P.G.M., and Greene T.W. Greene's Protective Groups in Organic Synthesis. 4th ed. (2007), Wiley, New York
31. For instance see:. Sondhi S.M., Rani R., Roy P., Agrawal S.K., and Saxena A.K. Bioorg. Med. Chem. Lett. 19 (2009) 1534-1538
32. Yunes J.A., Cardoso A.A., Yunes R.A., Correa R., de Campos-Buzzi F., and Cechinel F.V. Z. Naturforsch. 63c (2008) 675-680
33. Stewart S.G., Polomska M.E., and Lim R.W. Tetrahedron Lett. 48 (2007) 2241-2244
34. Kafi K., Betting D.J., Yamada R.E., Bacica M., Steward K.K., and Timmerman J.M. Mol. Immunol. 46 (2009) 448-456
35. Karim A.S., Johansson C.S., and Weltman J.K. Nucleic Acids Res. 23 (1995) 2037-2040
36. Wu M.-D., Cheng M.-J., Wang B.-C., Yech Y.-J., Lai J.-T., Kuo Y.-H., Yuan G.-F., and Chen I.-S. J. Nat. Prod. 71 (2008) 1258-1261
37. Wattanadilok R., Sawangwong P., Rodrigues C., Cidade H., Pinto M., Pinto E., Silva A., and Kijjoa A. Mar. Drugs 5 (2007) 40-51
38. Taveras, A. G.; Dwyer, M.; Ferreira, J. A.; Girijavallabhan, V. M.; Chao, J.; Baldwin, J. J.; Merritt, J. R.; Li, G. WO 2003031440.
39. Chandrasekhar S., Takhi M., and Uma G. Tetrahedron Lett. 38 (1997) 46, 8089-8092
40. Chandrasekhar S., Padmaja M.B., and Raza A. Synlett (1999) 1597-1599
41. General procedure for microwave-assisted synthesis of phthalimides (1): DMF (20 ml) solution of phthalic anhydride (1.5 g; 0.01 mol) and corresponding amine (0.01) were refluxed with magnetic stirring under microwave conditions as outlined in Table 1. The reaction mixture was poured onto crushed ice (∼200 g) and the formed white precipitate was separated by filtration, washed with water, and dried under reduced pressure. If necessary further purification was performed by column chromatography. General procedure for conventional synthesis of phthalimides in conventional method (1): To a suspension of phthalic anhydride (1 g; 6.8 mmol) and corresponding amine (0.85 mmol) in toluene (20 ml) triethylamine (1 ml) was added. The resulting reaction mixture was refluxed. After refluxing for time outlined in Table 1 the reaction mixture was concentrated to ∼1/4 cooled and the formed crystalline product was separated by filtration. If necessary column purification was performed.
42. Borah N.H., Boruah R.C., and Sandhu J.S. J. Chem. Res. (1998) 272-273
43. Pengo P., Pantos G.D., Otto S., and Sanders J.K.M. J. Org. Chem. 71 (2006) 7063-7066
44. Chapman Jr. J.M., Cocolas G.H., and Hall I.H. J. Med. Chem. 22 (1979) 1399-1402
45. Perry C.J., and Parveen Z. J. Chem. Soc., Perkin Trans. II (2001) 512-521
46. Khadilkar B.M., and Madyar V.R. Indian J. Chem. 41B (2002) 1083-1085
47. General procedure for the synthesis of 1,8-naphthalimides using a microwave (2 and 3): Pyridine or DMF (100 ml) solution of an anhydride (5 mmol) and corresponding amine were refluxed under microwave heating (Table 2). After cooling to room temperature, the reaction mixture was poured over ice. The formed white solid was separated by filtration. If necessary, the product was further purified by dissolving in dichloromethane, washing dichloromethane with water, and 10% hydrochloric acid. General procedure for conventional synthesis of 1,8-naphthalimides (2a, 2b and 3): A suspension of anhydride (5 mmol) and corresponding amine in pyridine (20 ml) or DMF (20 ml) was refluxed for several hours (Table 2). The reaction mixture was concentrated to about 1/4 and poured over ice. The formed crystalline product was separated by filtration.
48. General method for microwave-assisted synthesis of succinimides (4): DMF (20 ml) solution of succinic anhydride (2 g; 0.02 mol) and corresponding amine (0.015 mol) were refluxed in microwave reactor (magnetron power of 300 W) for 30 min. Into cooled reaction mixtures acetic anhydride (0.06 mol) was added and the reaction mixture was refluxed in microwave reactor for an additional 30 min. This was followed by the addition of water (5 ml) and microwave refluxed for 20 min. The reaction mixture was diluted with dichloromethane (100 ml), washed with saturated water solution of sodium bicarbonate (3 × 50 ml), water (3 × 50 ml), and dried over anhydrous sodium sulfate. After the solvent was evaporated, the crude product was purified by column chromatography with ethyl acetate-hexane (5:1) as an eluent. General method for conventional synthesis of succinimides (4). DMF (20 ml) solution of succinic anhydride (0.02 mol) and corresponding amine (0.015 mmol) was stirred at 50 °C for 30 min. Into this solution, acetic anhydride (5 ml) was added and the resulting reaction mixtures were refluxed under microwave for a few hours as specified in Table 3. After the refluxing reaction mixture was diluted with ice water (100 ml), it was stirred for 30 min and the product was isolated by dichloromethane extraction followed by column chromatography.
49. Kalgutkar A., Crews B.C., and Marnett L.J. J. Med. Chem. 39 (1996) 1692-1703
50. General procedure for the synthesis of maleimides 5: Tetrahydrofuran (20 ml) solution of maleic anhydride (0.01 mol) and tetrahydrofuran solution (20 ml) of corresponding amine (1.1 equiv) were mixed together and stirred at room temperature for 15 min. The solvent was decanted from white precipitate, and acetic anhydride (21 ml) and sodium acetate (1 g) were added to the solid material. The reaction mixture was heated with microwave magnetron power of 450 for 30 min. The reaction mixture was washed with ether (3 × 50 ml). After ether evaporation, the product was purified by column chromatography with 5% ethyl acetate in dichloromethane as an eluent.