Reaction on water: A greener approach for the thia michael addition on N-Aryl maleimides

Synthetic Communications

Volumn 41, Issue 3, 2011, Pages 392-404

  Kumar, Varun ^a   Mitra, Rangan ^a   Bhattarai, Sanjay ^a   Nair, Vipin A ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

N Aryl maleimides; thia Michael addition; thiols; water

Indexed keywords

1 (4 BROMOPHENYL) 3 (2 HYDROXYETHYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYL) 3 (4 BROMOPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYL) 3 (4 CHLOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYL) 3 (4 FLUOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYL) 3 (PYRIMIDIN 2 YLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYL) 3 PHENYLTHIOPYRROLIDINE 2,5 DIONE; 1 (4 BROMOPHENYLTHIO) 1 (4 FLUOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYL) 3 (2 HYDROXYETHYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYL) 3 (4 CHLOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYL) 3 (4 FLUOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYL) 3 (PYRIMIDIN 2 YLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYL) 3-PHENYLTHIOPYRROLIDINE 2,5 DIONE; 1 (4 CHLOROPHENYLTHIO) 3 (4 FLUOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 FLUOROPHENYL) 3 (2 HYDROXYETHYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 FLUOROPHENYL) 3 (4 FLUOROPHENYLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 FLUOROPHENYL) 3 (PYRIMIDIN 2 YLTHIO)PYRROLIDINE 2,5 DIONE; 1 (4 FLUOROPHENYL) 3 PHENYLTHIOPYRROLIDINE 2,5 DIONE; 3 (4 BROMOPHENYLTHIO) 1 (4 CHLOROPHENYL)PYRROLIDINE 2,5 DIONE; MALEIMIDE DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; GREEN CHEMISTRY; METHODOLOGY; MICHAEL ADDITION;

EID: 78751557301     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903576651     Document Type: Article

References (40)

1. (a) Coulter, D. A.; Huguenard, J. R.; Prince, D. A. Differential effects of petit mal anticonvulsants and convulsants on thalamic neurones: Calcium current reduction. Br. J. Pharmacol. 1990, 4, 800;
2. (b) Sami, S. M.; Dorr, R. T.; Alberts, D. S.; Solyom, A. M.; Remers, W. A. Analogues of amonafide and azonafide with novel ring systems. J. Med. Chem. 2000, 43, 3067;
3. (c) Wang, J. J.; Liu, T. Y.; Yin, P. H.; Wu, C. W.; Chern, Y. T.; Chi, C. W. Adamantyl maleimide induced changes in adhesion molecules and ROS are involved in apoptosis of human gastric cancer cells. Anticancer Res. 2000, 20, 3067;
4. (d) Rankin, G.; Cresseyv, K.; Wang, R.; Brown, P. Urinary tract effects of phensux-imide in the Sprage-Dawley and Fischer 344 rat. J. Appl. Toxicol. 1986, 6, 349;
5. (e) Miyachi, H.; Azuma, A.; Kitamoto, T.; Hayashi, K.; Kato, S.; Koga, M.; Sato, B.; Hashimoto, Y. Potent novel nonsteroidal androgen antagonist with a pthalimide skeleton. Bioorg. Med. Chem. Lett. 1997, 7, 1483.
6. Watanabe, N.; Che, F.; Iwano, M.; Takayama, S.; Naka, T.; Yoshida, S.; Isogai, A. Molecular characterization of photomixotrophic tobacco cells resistant to protopor-phyrinogen oxidase-inhibiting herbicide. Plant Physiol. 1998, 118, 751.
7. (a) Badawy, M. A.; Kadry, A. M.; Abdel, H.; Sayed, A.; Ibrahim, Y. A. Reinvestigation of the reactions of thiasemicarbazones with maleimides. Sulfur Lett. 1988, 8, 43;
8. (b) Mustafa, A.; Askar, W.; Khattab, S.; Mohmad, S.; Sayed, D. On the reactivity of the unsaturated system in N-arylmaleimides. J. Org. Chem. 1960, 26, 787.
9. Pastor, D. S.; Hessel, T. E.; Odorisio, A. P.; Spivack, D. J. 3-(4-Hydroxy-phenylthio)pyrroidine-2,5-diones. J. Heterocycl. Chem. 1985, 22, 1195.
10. (a) De Silva, F. M.; Gomes, A. K.; Jones, J. Jr. Organic reaction in water, part 2: Michael addition in water without phase transfer reagent. Can. J. Chem. 1999, 77, 624;
11. 3. Tetrahedron Lett. 2003, 44, 5115;
12. (c) Wabnitz, T. C.; Yu, J.-Q.; Spencer, J. B. A general, polymer-supported acid-catalyzed hetero-Michael addition. Synlett 2003, 1070;
13. (d) Cheng, S.; Comer, D. D. An alumina-catalyzed Michael addition of mercaptans to N-anilinomaleimides and its application to the solution-phase parallel synthesis of libraries. Tetrahedron Lett. 2002, 43, 1179;
14. (e) Zahouily, M.; Abrouki, Y.; Rayadh, A.; Sebti, S.; Dhimane, H.; David, M. Fluorapatite: Efficient catalyst for Michael addition. Tetrahedron Lett. 2003, 44, 2463;
15. 3-catalyzed 1,4- then 1,2-nucleophilic addition to enones. J. Org. Chem. 2002, 67, 3700;
16. 7, A new catalyst for Michael addition. Tetrahedron Lett. 2002, 43, 7729;
17. (h) Abrouki, Y.; Zahouily, M.; Rayadh, A.; Bahlaouan, B.; Sebti, S. A natural phosphate- and doped-catalyzed Michael addition of mercaptans to a,b-unsaturated carbonyl compounds. Tetrahedron Lett. 2002, 43, 8951;
18. (i) Kamimura, A.; Murakami, N.; Yokota, K.; Shirai, M.; Okamoto, H. Regioselective Michael addition of thiols to tertiary fumaric amide esters. Tetrahedron Lett. 2002, 43, 7521;
19. (j) Kangasabapathi, S.; Sudalai, A.; Benicewicz, B. C. Montmorillonite K-10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: An efficient synthesis of dithiocarboxylic esters. Tetrahedron Lett. 2001, 42, 3791;
20. (k) Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. A catalytic Michael addition of thiols to a,b-unsaturated carbonyl compounds: Asymmetric Michael additions and asymmetric protonations. J. Am. Chem. Soc. 1998, 120, 4043;
21. (l) Ahuja, P. R.; Natu, A. A.; Gogte, V. N. Optical induction, IV: Optical induction by using homogenous catalyst. Tetrahedron Lett. 1980, 21, 4743;
22. 2 as an extremely efficient, inexpensive, and reusable catalyst for chemoselective carbon-sulfur bond formation. Tetrahedron 2007, 63, 1200.
23. (a) Lee, C. H.; Lindsey, J. S. One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks. Tetrahedron 1994, 50, 11427;
24. (b) Jeon, K. O.; Jun, J. H.; Yu, J. S.; Lee, C. K. Infrared and nuclear magnetic resonance properties of benzoyl derivatives of five-membered monoheterocycles and determination of aromaticity indices. J. Heterocycl. Chem. 2003, 40, 763.
25. (a) Khatik, G. L.; Kumar, R.; Chakraborti, A. K. Catalyst-free conjugate addition of thiols to to a,b-unsaturated carbonyl compounds in water. Org. Lett. 2006, 8, 2433;
26. (b) Ranu, B. C; Dey, S. S.; Hajra, A. Catalysis by an ionic liquid: Efficient conjugate addition of thiols to electron-deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions. Tetrahedron 2003, 59, 2417;
27. 2O system. J. Org. Chem. 2003, 68, 7098;
28. (d) Ranu, B. C; Dey, S. S. Catalysis by ionic liquid: A simple, green, and efficient procedure for the Michael addition of thiols and thiophosphate to conjugated alkenes in ionic liquid, [pmIm]Br. Tetrahedron 2004, 60, 4183;
29. 3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles. Synthesis 2005, 2129;
30. 2O/NaI system supported on alumina in solvent-free conditions. J. Org. Chem. 2005, 70, 169;
31. (g) Shivani; Chakraborti, A. K. Zinc perchlorate hexa-hydrate as a new and highly efficient catalyst for synthesis of 2-hydroxysulfides by opening of epoxide rings with thiols under solvent-free conditions: Application for synthesis of the key intermediate of diltiazem. J. Mol Catal. A: Chem. 2007, 263, 137;
32. (h) Sharma, G.; Kumar, R.; Chakraborti, A. K. A novel environmentally friendly process for carbon-sulfur bond formation catalyzed by montmorillonite clays. J. Mol. Catal. A: Chem. 2007, 263, 143;
33. 2) as a new, highly efficient, and reusable heterogeneous catalyst for thia Michael addition to a,b-unsaturated carbonyl compounds. Tetrahedron Lett. 2008, 49, 4272;
34. (j) Chu, C.-M.; Tu, Z.; Wu, P.; Wang, C. C; Liu, J.-T.; Kuo, C-W.; Shin, Y.-H.; Yao, C.-F. Straightforward and highly efficient catalyst-free regioselective reaction of thiol to b-nitrostyrene: A concise synthesis of vinyl sulfide and nitro sulfide. Tetrahedron 2009, 65, 3878;
35. (k) Jose, R.; Perera, G.; Rotstein, B. H.; Thompson, A. Comparison of benzene, nitrobenzene, and dinitrobenzene 2-arylsulfenylpyrroles. J. Org. Chem. 2007, 72, 7382.
36. (a) Breslow, R.; Rideout, D. Hydrophobic acceleration of Diels-Alder reactions. J. Am. Chem. Soc. 1980, 102, 7816;
37. (b) Azizi, N.; Saidi, M. R. Highly chemoselective addition of amines to epoxides in water. Org. Lett. 2005, 7, 3649.
38. Klijn, J. E.; Engberts, J. B. Organic chemistry: Fast reactions "on water". Nature 2005, 435, 746.
39. Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. "On Water": Unique reactivity of organic compounds in aqueous suspension. Angew. Chem. Int. Ed. 2005, 44, 3275.
40. Blokzijl, W.; Blandamer, M. J.; Engberts, J. B. Diels-Alder reactions in aqueous solutions: Enforced hydrophobic interactions between diene and dienophile. J. Am. Chem. Soc. 1991, 113, 4241.