How to cite this paper
Borude, V., Shah, R & Shukla, S. (2013). Synthesis of B-amino alcohol derivatives from phenols in presence of phase transfer catalyst and lipase biocatalyst.Current Chemistry Letters, 2(1), 1-12.
Refrences
1. Erhardt, P. W., WOO, C. M., Gorczynski, R. J., and Anderson, W. G. (1982) Ultra-short-acting B-adrenergic receptor blocking agents. 1. (Ary1oxy) propanolamines containing esters in the nitrogen substituent. J. Med. Chem., 25, 1402-1407.
2. Kopka, K., Wagner, S., Riemann, B., Law, M. P., Puke, C., Luthra, S. K., Pike, V. W., Wichter, T., Schmitz, W., Schober, O., and Schafers, M. (2003) Design of new B1-selective adrenoceptor ligands as potential radioligands for in vivo imaging. Bioorg. Med. Chem., 11, 3513-3527.
3. Slater, R. A., Howson, W., Swayne, G. T. G., Taylor, E. M., and Reavill , D. R. (1988) Design and synthesis of a series of combined vasodilator/ B-adrenoceptor antagonists based on 6-arylpyridazinones. J. Med. Chem., 31, 345-351.
4. Gallego, L., and Arroyo, P. (2003) Determination of prednisolone, naphazoline, and phenylephrine in local pharmaceutical preparations by micellar electrokinetic chromatography. J. Sep. Sci., 26, 947-952.
5. Klingler, F. D. (2007) Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use. Acc. Chem. Res., 40, 1367-1376.
6. Castellano, M., and Bohm, M. (1997) The cardiac B-adrenoceptor–mediated signaling pathway and its alterations in hypertensive heart disease. Hypertension, 29, 715-722.
7. Yamada, S., Ohkura, T., Uchida, S., Inabe, K., Iwatani, Y., Kimura, R., Hoshino, T., and Kaburagi, T. (1996) A sustained increase in beta-adrenoceptors during long-term therapy with metoprolol and bisoprolol in patients with heart failure from idiopathic dilated cardiomyopathy. Life Sci., 58, 1737-1744.
8. Auvin-Guette, C., Rebuffat, S., Prigent, Y., and Bodo, B. (1992) Trichogin A IV, an 11-Residue lipopeptaibol from trichoderma longibrachiatum. J. Am. Chem. Soc., 114, 2170-2174.
9. Wright, J. L., Gregory, T. F., Heffner, T. G., Mackenzie, R. G., Pugsley, T. A., Meulen, S. V., and Wise, L. D. (1997) Discovery of selective dopamine d4 receptor antagonists: 1-aryloxy-3-(4-aryloxypiperidinyl)-2-propanols. Bioorg. Med. Chem., 7, 1377-1380.
10. Marquis, R. W., Lago, A. M., Callahan, J. F., Lee-Trout, R. E., Gowen, M., DelMar, E. G., Van-Wagenen, B. C., Logan, S., Shimizu, S., Fox, J., Nemeth, E. F., Yang, Z., Roethke, T., Smith, B. R., Ward, K. W., Lee, J., Keenan, R. M., and Bhatnagar, P. (2009) Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues. J. Med. Chem., 52, 3982-3993.
11. Apparu, M., Tiba, Y. B., Leo, P., Hamman, S., and Coulombeau, C. (2000) Determination of the enantiomeric purity and the configuration of B-amino alcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to B-blockers. Tetrahedron Asymmetry, 11, 2885-2898.
12. Joshi, R. A., Gurjar, M. K., and Tripathy, N. K. (2001) A new and improved process for celiprolol hydrochloride. Org. Process Res. Dev., 5, 176-178.
13. Cepanec, I., Litvic, M., Mikuldas, H., Bartolincic, A., and Vinkovic, V. (2003) Calcium trifluoromethanesulfonate-catalysed aminolysis of epoxides. Tetrahedron, 59, 2435-2439.
14. Yadav, J. S., Reddy, B. V. S., Basak, A. K., and Narsaiah, A. V. (2003) [Bmim]BF4 ionic liquid: a novel reaction medium for the synthesis of B-amino alcohols. Tetrahedron Lett., 44, 1047-1050.
15. Ollevier, T., and Lavie-Compin, G. (2004) Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions. Tetrahedron Lett., 45, 49-52.
16. Peukert, S., and Jacobsen, E. N. (1999) Enantioselective parallel synthesis using polymer-supported chiral Co(salen) complexes. Org. Lett., 1, 1245-1248.
17. Kantam, M. L., Neelima, B., Reddy, V., and Chakravarti, R. (2007) Aza-michael addition of imidazoles to ?,B-unsaturated compounds and synthesis of B-amino alcohols via nucleophilic ring opening of epoxides using copper(II)acetylacetonate (Cu(acac)2) immobilized in ionic liquids. Ind. Eng. Chem. Res., 46, 8614-8619.
18. Mojtahedi, M. M., Saidi, M. R., and Bolourtchian, M. (1999) Microwave-assisted aminolysis of epoxides under solvent-free conditions catalyzed by montmorillonite clay. J. Chem. Res. (S)., 128-129.
19. Pchelka, B. K., Loupy, A., and Petit, A. (2006) Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism. Tetrahedron, 62, 10968-10979.
20. Kazuhiro, K., Yoshiro, F., Hiroshi, Y., and Junzo, O. (1999) CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure B-blockers. Tetrahedron, 55, 14381-14390.
21. Fisher, L. G., Sher, P. M., Skwish, S., Michel, I. M., Seiler, S. M., and Dickinson, K. E. (1996) BMS-187257, a potent, selective, and novel heterocyclic B3-adrenergic receptor agonist. J. Bioorg. Med. Chem. Lett., 6, 2253-2258.
22. Sun, D., Scherman, M. S., Jones, V., Hurdle, J. G., Woolhiser, L. K., Knudson, S. E., Lenaerts, A. J., Slayden, R. A., McNeil, M. R., and Lee, R. E. (2009) Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity. Bioorg. Med. Chem., 17, 3588-3594.
23. Surendra, K., Srilakshmi-Krishnaveni, N., and Rama-Rao, K. (2005) The selective C-3 opening of aromatic 2,3-epoxy alcohols/epoxides with aromatic amines catalysed by B-cyclodextrin in water. Synlett, 3, 506-510.
24. Klibanov, A. M. (1986) Enzymes that work in organic solvents. Chemtech, 16, 354-359.
25. Pyo, S. H., Persson, P., Lundmark, S., and Hatti-Kaul, R. (2011) Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates. Green chem., 13, 976-982.
26. Sonawane, Y. A., Phadtare, S. B., Borse, B. N., Jagtap, A. R., and Shankarling, G. S. (2010) Synthesis of diphenylamine-based novel fluorescent styryl colorants by knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Org. Lett., 12, 1456-1459.
27. Li, K., He, T., Li, C., Feng, X. W., Wang, N., and Yu, X. Q. (2009) Lipase-catalysed direct mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a one-pot synthesis. Green Chem., 11, 777-779.
28. Fang, J. M., and Wong, C. H. (1994) Enzymes in organic synthesis: alteration of reversible reactions to irreversible processes. Synlett, 6, 393-402.
29. Starks, C. M. (1971) Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J. Am. Chem. Soc., 93, 195-199.
30. Hashimoto, T., and Maruoka, K. (2007) Recent development and application of chiral phase-transfer catalysts. Chem. Rev., 107, 5656-5682.
31. Hajipour, A. R., and Rafiee, F. (2009) Basic ionic liquids. A short review. J. Iran. Chem. Soc., 6, 647-678.
32. Ranu, B. C., and Banerjee, S. (2005) Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org. Lett., 7, 3049-3052.
33. Jiang, D., Wang, Y., Sun, H., and Dai, L. Y., (2007) Phase transfer reaction catalyzed by ionic liquids. J. Chil. Chem. Soc., 52, 1302-1304.
34. Yadav, G. D., and Motirale, B. G. (2008) Ionic liquid as catalyst for solid-liquid phase transfer catalyzed synthesis of p-nitrodiphenyl ether. Ind. Eng. Chem. Res., 47, 9081-9089.
35. Kim, D. W., and Chi, D. Y. (2004) Polymer-supported ionic liquids: imidazolium salts as catalysts for nucleophilic substitution reactions including fluorinations. Angew. Chem. Int. Ed., 43, 483-485;
36. Kim, D. W., Song, C. E., and Chi, D. Y. (2003) Significantly enhanced reactivities of the nucleophilic substitution reactions in ionic liquid. J. Org. Chem., 68, 4281-4285.
37. Xie, H., Zhang, S., and Duan, H. (2004) An ionic liquid based on a cyclic guanidinium cation is an efficient medium for the selective oxidation of benzyl alcohols. Tetrahedron Lett., 45, 2013-2015.
38. Kryshtal, G. V., Zhdankina, G. M., and Zlotin S. G. (2005) Tetraalkylammonium and 1,3-dialkylimidazolium salts with fluorinated anions as recoverable phase-transfer catalysts in solid base-promoted cross-aldol condensations. Eur. J. Org. Chem., 2822-2827.
39. Azizi, N., and Saidi, M. R. (2005) Highly chemoselective addition of amines to epoxides in water. Org. Lett., 7, 3649-3651.
40. Khadilkar, B. M., and Bendale, P. M. (1997) Microwave enhanced synthesis of epoxypropoxyphenols. Synth. Commun., 27, 2051-2056.
41. Borse, B. N., Borude, V. S., and Shukla, S. R. (2012) Synthesis of novel dihydropyrimidin-2(1H)-ones derivatives using lipase and their antimicrobial activity. Curr. Chem. Lett. 1, 47-58.
42. Harris, T. K., and Turner, G. J. (2002) Structural Basis of Perturbed pKa Values of Catalytic Groups in Enzyme Active Sites. IUBMB Life, 53, 85-98.
43. Palimkar, S. S., Siddiqui, S. A., Daniel, T., Lahoti R. J. and Srinivasan, K. V. (2003) Ionic liquid-promoted regiospecific friedlander annulation: novel synthesis of quinolines and fused polycyclic quinolines. J. Org. Chem., 68, 9371-9378.
2. Kopka, K., Wagner, S., Riemann, B., Law, M. P., Puke, C., Luthra, S. K., Pike, V. W., Wichter, T., Schmitz, W., Schober, O., and Schafers, M. (2003) Design of new B1-selective adrenoceptor ligands as potential radioligands for in vivo imaging. Bioorg. Med. Chem., 11, 3513-3527.
3. Slater, R. A., Howson, W., Swayne, G. T. G., Taylor, E. M., and Reavill , D. R. (1988) Design and synthesis of a series of combined vasodilator/ B-adrenoceptor antagonists based on 6-arylpyridazinones. J. Med. Chem., 31, 345-351.
4. Gallego, L., and Arroyo, P. (2003) Determination of prednisolone, naphazoline, and phenylephrine in local pharmaceutical preparations by micellar electrokinetic chromatography. J. Sep. Sci., 26, 947-952.
5. Klingler, F. D. (2007) Asymmetric hydrogenation of prochiral amino ketones to amino alcohols for pharmaceutical use. Acc. Chem. Res., 40, 1367-1376.
6. Castellano, M., and Bohm, M. (1997) The cardiac B-adrenoceptor–mediated signaling pathway and its alterations in hypertensive heart disease. Hypertension, 29, 715-722.
7. Yamada, S., Ohkura, T., Uchida, S., Inabe, K., Iwatani, Y., Kimura, R., Hoshino, T., and Kaburagi, T. (1996) A sustained increase in beta-adrenoceptors during long-term therapy with metoprolol and bisoprolol in patients with heart failure from idiopathic dilated cardiomyopathy. Life Sci., 58, 1737-1744.
8. Auvin-Guette, C., Rebuffat, S., Prigent, Y., and Bodo, B. (1992) Trichogin A IV, an 11-Residue lipopeptaibol from trichoderma longibrachiatum. J. Am. Chem. Soc., 114, 2170-2174.
9. Wright, J. L., Gregory, T. F., Heffner, T. G., Mackenzie, R. G., Pugsley, T. A., Meulen, S. V., and Wise, L. D. (1997) Discovery of selective dopamine d4 receptor antagonists: 1-aryloxy-3-(4-aryloxypiperidinyl)-2-propanols. Bioorg. Med. Chem., 7, 1377-1380.
10. Marquis, R. W., Lago, A. M., Callahan, J. F., Lee-Trout, R. E., Gowen, M., DelMar, E. G., Van-Wagenen, B. C., Logan, S., Shimizu, S., Fox, J., Nemeth, E. F., Yang, Z., Roethke, T., Smith, B. R., Ward, K. W., Lee, J., Keenan, R. M., and Bhatnagar, P. (2009) Antagonists of the calcium receptor I. Amino alcohol-based parathyroid hormone secretagogues. J. Med. Chem., 52, 3982-3993.
11. Apparu, M., Tiba, Y. B., Leo, P., Hamman, S., and Coulombeau, C. (2000) Determination of the enantiomeric purity and the configuration of B-amino alcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: application to B-blockers. Tetrahedron Asymmetry, 11, 2885-2898.
12. Joshi, R. A., Gurjar, M. K., and Tripathy, N. K. (2001) A new and improved process for celiprolol hydrochloride. Org. Process Res. Dev., 5, 176-178.
13. Cepanec, I., Litvic, M., Mikuldas, H., Bartolincic, A., and Vinkovic, V. (2003) Calcium trifluoromethanesulfonate-catalysed aminolysis of epoxides. Tetrahedron, 59, 2435-2439.
14. Yadav, J. S., Reddy, B. V. S., Basak, A. K., and Narsaiah, A. V. (2003) [Bmim]BF4 ionic liquid: a novel reaction medium for the synthesis of B-amino alcohols. Tetrahedron Lett., 44, 1047-1050.
15. Ollevier, T., and Lavie-Compin, G. (2004) Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions. Tetrahedron Lett., 45, 49-52.
16. Peukert, S., and Jacobsen, E. N. (1999) Enantioselective parallel synthesis using polymer-supported chiral Co(salen) complexes. Org. Lett., 1, 1245-1248.
17. Kantam, M. L., Neelima, B., Reddy, V., and Chakravarti, R. (2007) Aza-michael addition of imidazoles to ?,B-unsaturated compounds and synthesis of B-amino alcohols via nucleophilic ring opening of epoxides using copper(II)acetylacetonate (Cu(acac)2) immobilized in ionic liquids. Ind. Eng. Chem. Res., 46, 8614-8619.
18. Mojtahedi, M. M., Saidi, M. R., and Bolourtchian, M. (1999) Microwave-assisted aminolysis of epoxides under solvent-free conditions catalyzed by montmorillonite clay. J. Chem. Res. (S)., 128-129.
19. Pchelka, B. K., Loupy, A., and Petit, A. (2006) Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism. Tetrahedron, 62, 10968-10979.
20. Kazuhiro, K., Yoshiro, F., Hiroshi, Y., and Junzo, O. (1999) CsF in organic synthesis. Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure B-blockers. Tetrahedron, 55, 14381-14390.
21. Fisher, L. G., Sher, P. M., Skwish, S., Michel, I. M., Seiler, S. M., and Dickinson, K. E. (1996) BMS-187257, a potent, selective, and novel heterocyclic B3-adrenergic receptor agonist. J. Bioorg. Med. Chem. Lett., 6, 2253-2258.
22. Sun, D., Scherman, M. S., Jones, V., Hurdle, J. G., Woolhiser, L. K., Knudson, S. E., Lenaerts, A. J., Slayden, R. A., McNeil, M. R., and Lee, R. E. (2009) Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity. Bioorg. Med. Chem., 17, 3588-3594.
23. Surendra, K., Srilakshmi-Krishnaveni, N., and Rama-Rao, K. (2005) The selective C-3 opening of aromatic 2,3-epoxy alcohols/epoxides with aromatic amines catalysed by B-cyclodextrin in water. Synlett, 3, 506-510.
24. Klibanov, A. M. (1986) Enzymes that work in organic solvents. Chemtech, 16, 354-359.
25. Pyo, S. H., Persson, P., Lundmark, S., and Hatti-Kaul, R. (2011) Solvent-free lipase-mediated synthesis of six-membered cyclic carbonates from trimethylolpropane and dialkyl carbonates. Green chem., 13, 976-982.
26. Sonawane, Y. A., Phadtare, S. B., Borse, B. N., Jagtap, A. R., and Shankarling, G. S. (2010) Synthesis of diphenylamine-based novel fluorescent styryl colorants by knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Org. Lett., 12, 1456-1459.
27. Li, K., He, T., Li, C., Feng, X. W., Wang, N., and Yu, X. Q. (2009) Lipase-catalysed direct mannich reaction in water: utilization of biocatalytic promiscuity for C–C bond formation in a one-pot synthesis. Green Chem., 11, 777-779.
28. Fang, J. M., and Wong, C. H. (1994) Enzymes in organic synthesis: alteration of reversible reactions to irreversible processes. Synlett, 6, 393-402.
29. Starks, C. M. (1971) Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J. Am. Chem. Soc., 93, 195-199.
30. Hashimoto, T., and Maruoka, K. (2007) Recent development and application of chiral phase-transfer catalysts. Chem. Rev., 107, 5656-5682.
31. Hajipour, A. R., and Rafiee, F. (2009) Basic ionic liquids. A short review. J. Iran. Chem. Soc., 6, 647-678.
32. Ranu, B. C., and Banerjee, S. (2005) Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org. Lett., 7, 3049-3052.
33. Jiang, D., Wang, Y., Sun, H., and Dai, L. Y., (2007) Phase transfer reaction catalyzed by ionic liquids. J. Chil. Chem. Soc., 52, 1302-1304.
34. Yadav, G. D., and Motirale, B. G. (2008) Ionic liquid as catalyst for solid-liquid phase transfer catalyzed synthesis of p-nitrodiphenyl ether. Ind. Eng. Chem. Res., 47, 9081-9089.
35. Kim, D. W., and Chi, D. Y. (2004) Polymer-supported ionic liquids: imidazolium salts as catalysts for nucleophilic substitution reactions including fluorinations. Angew. Chem. Int. Ed., 43, 483-485;
36. Kim, D. W., Song, C. E., and Chi, D. Y. (2003) Significantly enhanced reactivities of the nucleophilic substitution reactions in ionic liquid. J. Org. Chem., 68, 4281-4285.
37. Xie, H., Zhang, S., and Duan, H. (2004) An ionic liquid based on a cyclic guanidinium cation is an efficient medium for the selective oxidation of benzyl alcohols. Tetrahedron Lett., 45, 2013-2015.
38. Kryshtal, G. V., Zhdankina, G. M., and Zlotin S. G. (2005) Tetraalkylammonium and 1,3-dialkylimidazolium salts with fluorinated anions as recoverable phase-transfer catalysts in solid base-promoted cross-aldol condensations. Eur. J. Org. Chem., 2822-2827.
39. Azizi, N., and Saidi, M. R. (2005) Highly chemoselective addition of amines to epoxides in water. Org. Lett., 7, 3649-3651.
40. Khadilkar, B. M., and Bendale, P. M. (1997) Microwave enhanced synthesis of epoxypropoxyphenols. Synth. Commun., 27, 2051-2056.
41. Borse, B. N., Borude, V. S., and Shukla, S. R. (2012) Synthesis of novel dihydropyrimidin-2(1H)-ones derivatives using lipase and their antimicrobial activity. Curr. Chem. Lett. 1, 47-58.
42. Harris, T. K., and Turner, G. J. (2002) Structural Basis of Perturbed pKa Values of Catalytic Groups in Enzyme Active Sites. IUBMB Life, 53, 85-98.
43. Palimkar, S. S., Siddiqui, S. A., Daniel, T., Lahoti R. J. and Srinivasan, K. V. (2003) Ionic liquid-promoted regiospecific friedlander annulation: novel synthesis of quinolines and fused polycyclic quinolines. J. Org. Chem., 68, 9371-9378.