Microwave-assisted, facile, rapid and solvent-free one pot two-component synthesis of some special acylals
English
Microwave-assisted, facile, rapid and solvent-free one pot two-component synthesis of some special acylals
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Key words:
- Double successive SN2 reactions
- / Acylal
- / Anilines
- / Methylene diester
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[1] (a) C.D. Hurd, S.M. Cantor, The analytical separation of various classes of sugars, J. Am. Chem. Soc. 60 (1938) 2677-2687;[1] (a) C.D. Hurd, S.M. Cantor, The analytical separation of various classes of sugars, J. Am. Chem. Soc. 60 (1938) 2677-2687;
-
[2]
(b) L.K. Sydnes, M. Sandberg, Aldehyde acylals-valuable compounds in synthesis when treated properly, PINSA 68 (2002) 141-174.(b) L.K. Sydnes, M. Sandberg, Aldehyde acylals-valuable compounds in synthesis when treated properly, PINSA 68 (2002) 141-174.
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[2] (a) B.B. Snider, S.G. Amin, An improved synthesis of 1α,3β-dihydroxycholesta- 5,7-diene, Synth. Commun. 8 (1978) 117-125;[2] (a) B.B. Snider, S.G. Amin, An improved synthesis of 1α,3β-dihydroxycholesta- 5,7-diene, Synth. Commun. 8 (1978) 117-125;
-
[4]
(b) G. Saucy, R. Marbet, H. Lindlar, O. Isler,Über eine neue synthese von citral und verwandten verbindungen, Helv. Chim. Acta 42 (1959) 1945-1955;(b) G. Saucy, R. Marbet, H. Lindlar, O. Isler,Über eine neue synthese von citral und verwandten verbindungen, Helv. Chim. Acta 42 (1959) 1945-1955;
-
[5]
(c) B.M. Trost, C.B. Lee, Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part II: scope and applications, J. Am. Chem. Soc. 123 (2001) 3687-3696;(c) B.M. Trost, C.B. Lee, Geminal dicarboxylates as carbonyl surrogates for asymmetric synthesis. Part II: scope and applications, J. Am. Chem. Soc. 123 (2001) 3687-3696;
-
[6]
(d) J.G. Frick, R.J. Harper, Acetals as crosslinking reagents for cotton, J. Appl. Polym. Sci. 29 (1984) 1433-1447;(d) J.G. Frick, R.J. Harper, Acetals as crosslinking reagents for cotton, J. Appl. Polym. Sci. 29 (1984) 1433-1447;
-
[7]
(e) V.T. Kamble, V.S. Jamode, An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2), Tetrahedron Lett. 47 (2006) 5573-5576.(e) V.T. Kamble, V.S. Jamode, An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2), Tetrahedron Lett. 47 (2006) 5573-5576.
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[3] L.K. Sydnes, M. Sandberg, The chemistry of acylals. Part I. The reactivity of acylals towards grignard and organolithium reagents, Tetrahedron 53 (1997) 12679- 12690.[3] L.K. Sydnes, M. Sandberg, The chemistry of acylals. Part I. The reactivity of acylals towards grignard and organolithium reagents, Tetrahedron 53 (1997) 12679- 12690.
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[4] (a) J.M. Thomas, Uniform heterogeneous catalysts: the role of solid-state chemistry in their development and design, Angew. Chem. Int. Ed. Engl. 27 (1988) 1673-1691;[4] (a) J.M. Thomas, Uniform heterogeneous catalysts: the role of solid-state chemistry in their development and design, Angew. Chem. Int. Ed. Engl. 27 (1988) 1673-1691;
-
[10]
(b) M.D. Carrigan, K.J. Eash, M.C. Oswald, R.S. Mohan, An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate, Tetrahedron Lett. 42 (2001) 8133-8135;(b) M.D. Carrigan, K.J. Eash, M.C. Oswald, R.S. Mohan, An efficient method for the chemoselective synthesis of acylals from aromatic aldehydes using bismuth triflate, Tetrahedron Lett. 42 (2001) 8133-8135;
-
[11]
(c) M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Nocchetti, Preparation and deprotection of 1,1-diacetates (acylals) using zirconium sulfophenyl phosphonate as catalyst, Tetrahedron Lett. 43 (2002) 2709-2711.(c) M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Nocchetti, Preparation and deprotection of 1,1-diacetates (acylals) using zirconium sulfophenyl phosphonate as catalyst, Tetrahedron Lett. 43 (2002) 2709-2711.
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[5] (a) P. Kumar, V.R. Hegde, T.P. Kumar, An efficient synthsis of diacetates from aldehydes using beta zeolite, Tetrahedron Lett. 4 (1995) 601-603;[5] (a) P. Kumar, V.R. Hegde, T.P. Kumar, An efficient synthsis of diacetates from aldehydes using beta zeolite, Tetrahedron Lett. 4 (1995) 601-603;
-
[13]
(b) Y. Ishino, M. Mihara, Zinc-metal promoted selective a-haloacylation and gembisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane, Tetrahedron Lett. 45 (2004) 3503-3506.(b) Y. Ishino, M. Mihara, Zinc-metal promoted selective a-haloacylation and gembisacylation of alkyl aldehydes in the presence of chlorotrimethylsilane, Tetrahedron Lett. 45 (2004) 3503-3506.
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[6] (a) H. Hopff, G. Hegar, Reaktionen des kohlensuboxids mit carbonylverbindungen, HeIv. Chim. Acta 44 (1961) 2016-2021; (b) D.A. Upson, V.J. Hruby, Synthesis of specifically deuterated S-benzylcysteines and of oxytocin and related diastereomers deuterated in the half-cystine positions, J. Org. Chem. 41 (1976) 1353-1358.[6] (a) H. Hopff, G. Hegar, Reaktionen des kohlensuboxids mit carbonylverbindungen, HeIv. Chim. Acta 44 (1961) 2016-2021; (b) D.A. Upson, V.J. Hruby, Synthesis of specifically deuterated S-benzylcysteines and of oxytocin and related diastereomers deuterated in the half-cystine positions, J. Org. Chem. 41 (1976) 1353-1358.
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[7] (a) N. Deka, D.J. Kalita, R. Borah, J.C. Sarma, Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes, J. Org. Chem. 62 (1997) 1563-1564;[7] (a) N. Deka, D.J. Kalita, R. Borah, J.C. Sarma, Iodine as acetylation catalyst in the preparation of 1,1-diacetates from aldehydes, J. Org. Chem. 62 (1997) 1563-1564;
-
[16]
(b) R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, Indium triflate: a reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals, J. Mol. Catal. 215 (2004) 49-53;(b) R. Ghosh, S. Maiti, A. Chakraborty, R. Halder, Indium triflate: a reusable catalyst for expeditious chemoselective conversion of aldehydes to acylals, J. Mol. Catal. 215 (2004) 49-53;
-
[17]
(c) B. Karimi, J. Maleki, Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions, J. Org. Chem. 68 (2003) 4951-4953.(c) B. Karimi, J. Maleki, Lithium trifluoromethanesulfonate (LiOTf) as a recyclable catalyst for highly efficient acetylation of alcohols and diacetylation of aldehydes under mild and neutral reaction conditions, J. Org. Chem. 68 (2003) 4951-4953.
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[8] K. Holmberg, B. Hansen, Methylene diesters of carboxylic acids from dichloromethane, Tetrahedron Lett. 27 (1975) 2303-2306.[8] K. Holmberg, B. Hansen, Methylene diesters of carboxylic acids from dichloromethane, Tetrahedron Lett. 27 (1975) 2303-2306.
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[9] Z.G. Luo, Y. Zhao, F. Xu, Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K2CO3 catalyzed 1,3-dipolarcycloaddition reaction, Chin. Chem. Lett. 25 (2014) 1346-1348.[9] Z.G. Luo, Y. Zhao, F. Xu, Synthesis and thermal properties of novel calix[4]arene derivatives containing 1,2,3-triazole moiety via K2CO3 catalyzed 1,3-dipolarcycloaddition reaction, Chin. Chem. Lett. 25 (2014) 1346-1348.
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[10] J.H. Xue, X.H. Hua, L.M. Yang, Synthesis, crystal structures and luminescence properties of europium and terbium picolinamide complexes, Chin. Chem. Lett. 25 (2014) 887-891.[10] J.H. Xue, X.H. Hua, L.M. Yang, Synthesis, crystal structures and luminescence properties of europium and terbium picolinamide complexes, Chin. Chem. Lett. 25 (2014) 887-891.
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[11] A.L. Cimecioglu, G.C. East, The synthesis of cyclic methylene dicarboxylates from caesium dicarboxylates and dibromomethane, Makromol. Chem. Rapid Commun. 8 (1987) 141-146.[11] A.L. Cimecioglu, G.C. East, The synthesis of cyclic methylene dicarboxylates from caesium dicarboxylates and dibromomethane, Makromol. Chem. Rapid Commun. 8 (1987) 141-146.
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