An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate
English
An efficient one-pot multi-component synthesis of 3,4,5-substituted furan-2(5H)-ones catalyzed by tetra-n-butylammonium bisulfate
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[1] F.A.Dean, Naturally Occurring Oxygen Ring Compounds, Butterworth, London, 1963.[1] F.A.Dean, Naturally Occurring Oxygen Ring Compounds, Butterworth, London, 1963.
-
[2] K. Nakanishi, T. Goto, S. Ito, S. Natori, S. Nozoe (Eds.), Natural Products Chemistry, vols. 1-3, Kodansha, Tokyo, 1974.[2] K. Nakanishi, T. Goto, S. Ito, S. Natori, S. Nozoe (Eds.), Natural Products Chemistry, vols. 1-3, Kodansha, Tokyo, 1974.
-
[3] F.M. Dean, Recent advances in furan chemistry. Part Ⅱ, in: A.R. Katritzky (Ed.), Advances in Heterocyclic Chemistry, vol. 31, Academic Press,NewYork, 1983, p.237.[3] F.M. Dean, Recent advances in furan chemistry. Part Ⅱ, in: A.R. Katritzky (Ed.), Advances in Heterocyclic Chemistry, vol. 31, Academic Press,NewYork, 1983, p.237.
-
[4] M.V. Sargent, F.M. Dean, Furans and their benzo derivatives: (ii) reactivity, in: C.W. Bird, G.W.H. Cheeseman (Eds.), Comprehensive Heterocyclic Chemistry, vol. 3, Pergamon Press, Oxford, 1984, p. 599.[4] M.V. Sargent, F.M. Dean, Furans and their benzo derivatives: (ii) reactivity, in: C.W. Bird, G.W.H. Cheeseman (Eds.), Comprehensive Heterocyclic Chemistry, vol. 3, Pergamon Press, Oxford, 1984, p. 599.
-
[5] B.H. Lipshutz, Five-membered heteroaromatic rings as intermediates in organic synthesis, Chem. Rev. 86 (1986) 795-819.[5] B.H. Lipshutz, Five-membered heteroaromatic rings as intermediates in organic synthesis, Chem. Rev. 86 (1986) 795-819.
-
[6] I. Bock, H. Bornowski, A. Ranft, H. Theis, New aspects in the synthesis of mono-and dialkylfurans, Tetrahedron 46 (1990) 1199-1210.[6] I. Bock, H. Bornowski, A. Ranft, H. Theis, New aspects in the synthesis of mono-and dialkylfurans, Tetrahedron 46 (1990) 1199-1210.
-
[7] D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, et al., Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor a, J. Med. Chem. 44 (2001) 3838-3848.[7] D.S. Mortensen, A.L. Rodriguez, K.E. Carlson, et al., Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor a, J. Med. Chem. 44 (2001) 3838-3848.
-
[8] M. Naim, I. Zuker, U. Zehavi, R.L. Rouseff, Inhibition by thiol compounds of offflavor formation in stored orange juice 2. Effect of L-cysteine and N-acetyl-Lcysteine on p-vinylguaiacol formation, J. Agric. Food Chem. 41 (1993) 1359-1361.[8] M. Naim, I. Zuker, U. Zehavi, R.L. Rouseff, Inhibition by thiol compounds of offflavor formation in stored orange juice 2. Effect of L-cysteine and N-acetyl-Lcysteine on p-vinylguaiacol formation, J. Agric. Food Chem. 41 (1993) 1359-1361.
-
[9] R. Benassi, Furans and their benzo derivatives: structure, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 259.[9] R. Benassi, Furans and their benzo derivatives: structure, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 259.
-
[10] H. Heaney, J.S. Ahn, Furans and their benzo derivatives: reactivity, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 29, Pergamon Press, Oxford, 1996, p. 297.[10] H. Heaney, J.S. Ahn, Furans and their benzo derivatives: reactivity, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 29, Pergamon Press, Oxford, 1996, p. 297.
-
[11] W. Friedrichsen, Furans and their benzo derivatives: synthesis, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 351.[11] W. Friedrichsen, Furans and their benzo derivatives: synthesis, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 351.
-
[12] B.A. Keay, P.W. Dibble, Furans and their benzo derivatives: applications, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 395.[12] B.A. Keay, P.W. Dibble, Furans and their benzo derivatives: applications, in: A.R. Katritzky, C.W. Rees, E.F.V. Scriven (Eds.), Comprehensive Heterocyclic Chemistry Ⅱ, vol. 2, Pergamon Press, Oxford, 1996, p. 395.
-
[13] B.M. Trost, I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991.[13] B.M. Trost, I. Fleming, Comprehensive Organic Synthesis, Pergamon Press, Oxford, 1991.
-
[14] A.I. Meyers, Heterocycles in Organic Synthesis, Wiley-Interscience, New York, 1974.[14] A.I. Meyers, Heterocycles in Organic Synthesis, Wiley-Interscience, New York, 1974.
-
[15] X.L. Hou, Z. Yang, H.N.C. Wong, Five-membered ring systems: furans and benzofurans, in: G.W. Gribble, T.L. Gilchrist (Eds.), The Structure, Reactions, Synthesis, and Uses of Heterocyclic Compounds, Progress in Heterocyclic Chemistry, vol. 14, Pergamon Press, Oxford, 2002, p. 139.[15] X.L. Hou, Z. Yang, H.N.C. Wong, Five-membered ring systems: furans and benzofurans, in: G.W. Gribble, T.L. Gilchrist (Eds.), The Structure, Reactions, Synthesis, and Uses of Heterocyclic Compounds, Progress in Heterocyclic Chemistry, vol. 14, Pergamon Press, Oxford, 2002, p. 139.
-
[16] X.L. Hou, H.Y. Cheung, T.Y. Hon, et al., Regioselective syntheses of substituted furans, Tetrahedron 54 (1998) 1955-2020.[16] X.L. Hou, H.Y. Cheung, T.Y. Hon, et al., Regioselective syntheses of substituted furans, Tetrahedron 54 (1998) 1955-2020.
-
[17] R. Cao, C. Liu, L. Liu, A convenient synthesis of 2(5H)-furanose, Org. Prep. Proc. Int. 28 (1996) 215-216.[17] R. Cao, C. Liu, L. Liu, A convenient synthesis of 2(5H)-furanose, Org. Prep. Proc. Int. 28 (1996) 215-216.
-
[18] C. Fu, S. Ma, Efficient preparation of 4-iodofuran-2(5H)-ones by iodolactonisation of 2,3-allenoates with I2, Eur. J. Org. Chem. 2005 (2005) 3942-3945.[18] C. Fu, S. Ma, Efficient preparation of 4-iodofuran-2(5H)-ones by iodolactonisation of 2,3-allenoates with I2, Eur. J. Org. Chem. 2005 (2005) 3942-3945.
-
[19] (a) G.J. Hollingworth, G. Perkins, J.B. Sweeney, Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones, J. Chem. Soc. Perkin Trans. 1 (1996) 1913-1917;[19] (a) G.J. Hollingworth, G. Perkins, J.B. Sweeney, Preparation and palladium-catalysed cross-coupling reactions of 3-and 4-tributylstannylfuran-2(5H)-ones, J. Chem. Soc. Perkin Trans. 1 (1996) 1913-1917;
-
[20]
(b) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bis(tributylstannyl)-2(5H)-furanone, J. Org. Chem. 64 (1999) 328-329;(b) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bis(tributylstannyl)-2(5H)-furanone, J. Org. Chem. 64 (1999) 328-329;
-
[21]
(c) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bisstannyl-2(5H)furanones, Tetrahedron 58 (2002) 9117-9129.(c) R. Mabon, A.M.E. Richecoeur, J.B. Sweeney, Preparation and reactions of 3,4-bisstannyl-2(5H)furanones, Tetrahedron 58 (2002) 9117-9129.
-
[20] M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Synthesis of a,b-unsaturated 4, 5-disubstituted g-lactones via ring-closing metathesis catalyzed by the firstgeneration Grubbs' catalyst, Org. Lett. 7 (2005) 1805-1808.[20] M. Bassetti, A. D'Annibale, A. Fanfoni, F. Minissi, Synthesis of a,b-unsaturated 4, 5-disubstituted g-lactones via ring-closing metathesis catalyzed by the firstgeneration Grubbs' catalyst, Org. Lett. 7 (2005) 1805-1808.
-
[21] S. Narayana Murthy, B. Madhav, A. Vijay Kumar, K. Rama Rao, Y.V.D. Nageswar, Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using bcyclodextrin as reusable catalyst, Tetrahedron 65 (2009) 5251-5256.[21] S. Narayana Murthy, B. Madhav, A. Vijay Kumar, K. Rama Rao, Y.V.D. Nageswar, Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using bcyclodextrin as reusable catalyst, Tetrahedron 65 (2009) 5251-5256.
-
[22] R. Subburethinam, N. Rajagopal, Efficient one-pot multicomponent synthesis of (carbazolylamino)furan-2(5H)-one and carbazolyltetrahydropyrimidine derivatives, Synthesis 20 (2011) 3307-3317.[22] R. Subburethinam, N. Rajagopal, Efficient one-pot multicomponent synthesis of (carbazolylamino)furan-2(5H)-one and carbazolyltetrahydropyrimidine derivatives, Synthesis 20 (2011) 3307-3317.
-
[23] L. Nagarapu, U. Nikhil Kumar, P. Upendra, R. Bantu, Simple, convenient method for the synthesis of substituted furan-2(5H)-one derivatives using Tin(Ⅱ) chloride, Synth. Commun. 42 (2012) 2139-2148.[23] L. Nagarapu, U. Nikhil Kumar, P. Upendra, R. Bantu, Simple, convenient method for the synthesis of substituted furan-2(5H)-one derivatives using Tin(Ⅱ) chloride, Synth. Commun. 42 (2012) 2139-2148.
-
[24] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, Acetic acid as an efficient catalyst for the one-pot preparation of 3,4,5-substituted furan-2(5H)-ones, Res. Chem. Intermed. (2013), http://dx.doi.org/10.1007/s11164-012-0922-1 (This article is being published).[24] R. Doostmohammadi, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, Acetic acid as an efficient catalyst for the one-pot preparation of 3,4,5-substituted furan-2(5H)-ones, Res. Chem. Intermed. (2013), http://dx.doi.org/10.1007/s11164-012-0922-1 (This article is being published).
-
[25] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, g-Spiroiminolactone synthesis by reaction of acetylenic esters and a-dicarbonyl compounds in the presence of aryl isocyanide, Synth. Commun. 35 (2005) 2771-2777.[25] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, g-Spiroiminolactone synthesis by reaction of acetylenic esters and a-dicarbonyl compounds in the presence of aryl isocyanide, Synth. Commun. 35 (2005) 2771-2777.
-
[26] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Reaction of alkyl and aryl Isocyanides with floren-9-ones in the presence of acetylenic esters: preparation of g-spiroiminolactones, Synth. Commun. 35 (2005) 2569-2574.[26] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Reaction of alkyl and aryl Isocyanides with floren-9-ones in the presence of acetylenic esters: preparation of g-spiroiminolactones, Synth. Commun. 35 (2005) 2569-2574.
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[27] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, 1, 8-Diazafloren-9-one with alkyl and aryl isocyanides in the presence of acetylenic esters: a facile synthesis of g-spiroiminolactones, J. Heterocycl Chem. 43 (2006) 481-484.[27] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, G. Marandi, M. Nassiri, 1, 8-Diazafloren-9-one with alkyl and aryl isocyanides in the presence of acetylenic esters: a facile synthesis of g-spiroiminolactones, J. Heterocycl Chem. 43 (2006) 481-484.
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[28] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., g-Dispiro-iminolactone synthesis by three component reaction between alkyl isocyanides and acetylenic esters with a-dicarbonyl compounds, ARKIVOC xiii (2007) 34-40.[28] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., g-Dispiro-iminolactone synthesis by three component reaction between alkyl isocyanides and acetylenic esters with a-dicarbonyl compounds, ARKIVOC xiii (2007) 34-40.
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[29] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., Synthesis of novel 2-pyridylsubstituted 2,5-dihydro-2-imino-and 2-amino-furan derivatives via a three component condensation of alkyl isocyanides and acetylenic esters with di-(2-pyridyl) ketone or 2-pyridinecarboxaldehyde, ARKIVOC i (2007) 173-179.[29] N. Hazeri, M.T. Maghsoodlou, R. Heydari, et al., Synthesis of novel 2-pyridylsubstituted 2,5-dihydro-2-imino-and 2-amino-furan derivatives via a three component condensation of alkyl isocyanides and acetylenic esters with di-(2-pyridyl) ketone or 2-pyridinecarboxaldehyde, ARKIVOC i (2007) 173-179.
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[30] F. Rostami-Charati, M.T. Maghsoodlou, S.M. Habibi Khorassani, R. Heydari, M. Makha, Green diastereoselective synthesis of highly functionalised trifluoromethylated c-lactone phosphonate esters bearing a thioester or ketothiophene, Tetrahedron Lett. 49 (2008) 343-347.[30] F. Rostami-Charati, M.T. Maghsoodlou, S.M. Habibi Khorassani, R. Heydari, M. Makha, Green diastereoselective synthesis of highly functionalised trifluoromethylated c-lactone phosphonate esters bearing a thioester or ketothiophene, Tetrahedron Lett. 49 (2008) 343-347.
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[31] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Diastereoselective synthesis of g-ispiroiminolactone bearing naphthalene or bipyridine pendant groups, J. Heterocycl. Chem. 46 (2009) 843-848.[31] M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, et al., Diastereoselective synthesis of g-ispiroiminolactone bearing naphthalene or bipyridine pendant groups, J. Heterocycl. Chem. 46 (2009) 843-848.
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[32] M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, et al., One-pot threecomponent synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles, Tetrahedron 67 (2011) 8492-8495.[32] M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Moradi, et al., One-pot threecomponent synthesis of functionalized spirolactones by means of reaction between aromatic ketones, dimethyl acetylenedicarboxylate, and N-heterocycles, Tetrahedron 67 (2011) 8492-8495.
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[33] M.T. Maghsoodlou, G. Marandi, N. Hazeri, S.M. Habibi-Khorassani, A.A. Mirzaei, Synthesis of 5-aryl-1,3-dimethyl-6-(alkyl-or aryl-amino)furo[2,3-d] pyrimidine derivatives by reaction between isocyanides and pyridinecarbaldehydes in the presence of 1,3-dimethylbarbituric acid,Mol. Divers. 15 (2011) 227-231.[33] M.T. Maghsoodlou, G. Marandi, N. Hazeri, S.M. Habibi-Khorassani, A.A. Mirzaei, Synthesis of 5-aryl-1,3-dimethyl-6-(alkyl-or aryl-amino)furo[2,3-d] pyrimidine derivatives by reaction between isocyanides and pyridinecarbaldehydes in the presence of 1,3-dimethylbarbituric acid,Mol. Divers. 15 (2011) 227-231.
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