Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions

Synthetic Communications

Volumn 43, Issue 11, 2013, Pages 1571-1576

  Neves Filho, Ricardo A W ^a   Palm Forster, Mieder A T ^b   De Oliveira, Ronaldo N ^a  

^a UNIVERSIDADE FEDERAL RURAL DE PERNAMBUCO   (Brazil)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Imidazole; Phthalimide; Solventless; Urea

Indexed keywords

IMIDAZOLE; N,N' DISUBSTITUTED UREA; PHTHALIMIDE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; THERMAL ANALYSIS;

EID: 84876237140     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.651677     Document Type: Article

References (30)

1. Sharma, U.; Kumar, P.; Kumar, N.; Singh, B. Recent advances in the chemistry of Phthalimide analogues and their therapeutic potential. Mini-Rev. Med. Chem. 2010, 10, 678-704.
2. Alexandre-Moreira, M. S.; Takiya, C. M.; de Arruda, L. B.; Pascarelli, B.; Gomes, R. N.; Faria Neto, H. C. C.; Lima, L. M.; Barreiro, E. J. LASSBio-468: A new achiral thalidomide analogue which modulates TNF-a and NO production and inhibits endotoxic shock and arthritis in an animal model. Int. Immunopharmacol. 2005, 5, 485-494 (Pubitemid 40430756)
3. Baskin, C. B.; Baskin, J. M. Seeds: Ecology, Biogeography, and Evolution of Dormancy and Germination; Academic Press: San Diego, CA, 2001.
4. (a) Chapman, J. M.; Cocolas, G. H.; Hall, I. H. Hypolipidemic activity of phthalimide derivatives, 1: N-Substituted phthalimide derivatives. J. Med. Chem. 1979, 22, 1399-1402; (Pubitemid 10193610)
5. (b) Sena, V. L.; Srivastava, R. M.; Silva, R. O.; Lima, V. L. Synthesis and hypolipidemic activity of N-substituted phthalimides, part V. Farmaco 2003, 58, 1283-1288. (Pubitemid 37433853)
6. Orzeszko, A.; Kaminska, B.; Starosciak, B. J. Synthesis and antimicrobial activity of new adamantane derivatives III. Farmaco 2002, 57, 619-624. (Pubitemid 34876987)
7. Teisseire, H.; Vernet, G. Effects of the fungicide folpet on the activities of antioxidative enzymes in duckweed (Lemna minor). Pestic. Biochem. Physiol. 2001, 69, 112-117. (Pubitemid 32901078)
8. (a) Wiecek, M.; Kiec-Kononowicz, K. Synthesis and anticonvulsant evaluation of some N-substituted phthalimides. Acta Poloniae Pharmaceut. 2009, 66, 249-257;
9. (b) Vamecq, J.; Lambert, D.; Poupaert, J. H.; Masereel, B.; Stables, J. P. Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogues of ameltolide. J. Med. Chem. 1998, 41, 3307-3313. (Pubitemid 28406537)
10. Casaban-Ros, E.; Anton-Fos, G. M.; Galvez, J.; Duart, M. J.; Garcia-Domenech, R. Search for new antihistaminic compounds by molecular connectivity. Quant. Struct.-Act. Relat. 1999, 18, 35-42. (Pubitemid 29132531)
11. Shinji, C.; Nakamura, T.; Maeda, S.; Yoshida, M.; Hashimoto, Y.; Miyachi, H. Design and synthesis of phthalimide-type histone deacetylase inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 4427-4431. (Pubitemid 41253869)
12. Ungwitayatorn, J.; Wiwat, C.; Matayatsuk, C.; Pimthon, J.; Piyaviriyakul, S. Synthesis and HIV-1 reverse transcriptase inhibitory activity of non-nucleoside phthalimide derivatives. Chin. J. Chem. 2008, 26, 379-387.
13. Bialecka-Florjanczyk, E.; Melon-Ksyta, D.; Orzeszko, A.; Sledzinska, I.; Przedmojski, J.; Gorecka, E. Studies on the liquid crystalline behaviour of novel N-alkyl-substituted ester imides. Liquid Cryst. 2004, 31, 1227-1234.
14. (a) Muhlbacher, D.; Brabec, C. J.; Sariciftci, N. S.; Kotov, B. V.; Berendyaev, V. I.; Rumyantsev, B. M.; Hummelen, J. C. Sensitization of photoconductive polyimides for photovoltaic applications. Syntn. Met. 2001, 121, 1609-1610; (Pubitemid 32486312)
15. (b) Yan, S. F.; Belov, V. N.; Bossi,M. L.; Hell, S. W. Switchable fluorescent and solvatochromic molecular probes based on 4-amino-N- methylphthalimide and a photochromic diarylethene. Eur. J. Org. Chem. 2008, 2531-2538.
16. Howell, R. C.; Edwards, S. H.; Gajadhar-Plummer, A. S.; Kahwa, I. A.; McPherson, G. L.; Mague, J. T.; White, A. J. P.; Williams, D. J. Phthalimides: Supramolecular interactions in crystals, hypersensitive solution H-1-NMR dynamics and energy transfer to europium(III) and terbium(III) states. Molecules 2003, 8, 565-592. (Pubitemid 38990157)
17. Barbosa, F. C. G.; de Oliveira, R. N. Synthesis of a new class of triazole-linked benzoheterocycles via 1,3-dipolar cycloaddition. J. Braz. Chem. Soc. 2011, 22, 592-597.
18. Vasilevskaya, T. N.; Yakovleva, O. D.; Kobrin, V. S. A convenient method of N-methylphthalimide synthesis. Synth. Commun. 1995, 25, 2463-2465.
19. Liang, J.; Lv, J.; Fan, J. C.; Shang, Z. C. Polyethylene glycol as a nonionic liquid solvent for the synthesis of N-alkyl and N-arylimides. Synth. Commun. 2009, 39, 2822-2828.
20. Li, H. Z.; Zhang, J. S.; Zhou, Y. M.; Li, T. S. A rapid synthesis of N-aryl phthalimides under microwave irradiation in the absence of solvent. Synth. Commun. 2002, 32, 927-930.
21. Zonta, C.; De Lucchi, O.; Linden, A.; Lutz, M. Synthesis and structure of D-3hsymmetric triptycene trimaleimide. Molecules 2010, 15, 226-232.
22. Neves, R. A. W.; de Oliveira, R. N.; Srivastava, R. M. Microwave-mediated and customary synthesis of N-benzoyl- or N-substituted benzoyl-N,N0- dialkylureas from arylcarboxylic acids and N,N0-disubstituted carbodiimides under solvent-free conditions. J. Braz. Chem. Soc. 2007, 18, 1410-1414.
23. Neves, R. A. W. Urea: A useful and inexpensive chemical for organic synthesis. Synlett 2008, 2552-2553.
24. Schaber, P. A.; Colson, J.; Higgins, S.; Thielen, D.; Anspach, B.; Brauer, J. Thermal decomposition (pyrolysis) of urea in an open reaction vessel. Thermochim. Acta 2004, 424, 131-142.
25. Estiu, G.; Merz, K. M. Catalyzed decomposition of urea: Molecular dynamics simulations of the binding of urea to urease. Biochem. 2006, 45, 4429-4443.
26. (a) Baldwin, B. W.; Hirose, T.; Wang, Z. H. Improved microwave oven synthesis of amides and imides promoted by imidazole: Convenient transport agent preparation. Chem. Commun. 1996, 2669-2670; (Pubitemid 126442209)
27. (b) Neves, R. A. W.; Srivastava, R. M. A handy and solventless direct route to primary 3-[3-aryl)-1,2,4-oxadiazol-5-yl]propionamides using microwave irradiation. Molecules 2006, 11, 318-324. (Pubitemid 44651278)
28. Pasha, M. A.; Jayashankara, V. P. Efficient synthesis of N,N0-disubstituted ureas=thioureas catalyzed by iodine. Synth. Commun. 2006, 36, 1787-1793.
29. Shvydkiv, O.; Gallagher, S.; Nolan, K.; Oelgemoller, M. From conventional to microphotochemistry: Photodecarboxylation reactions involving phthalimides. Org. Lett. 2010, 12, 5170-5173.
30. Hsieh, J.-C.; Cheng, C. H. Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: A novel method for the synthesis of imide and amide derivatives. Chem. Commun. 2005, 4554-4556. (Pubitemid 41428444)