Microwave Mediated Dearylation of 2-Aryloxy-5-Nitropyridine

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Microwave Mediated Dearylation of 2-Aryloxy-5-Nitropyridine

Author Affiliations

¹Department of Medicinal Chemistry, Piramal Life Sciences Limited, 1Nirlon Complex, Goregaon East, Mumbai 400063, INDIA

Res.J.chem.sci., Volume 1, Issue (6), Pages 84-87, September,18 (2011)

Abstract

2-aryloxy-5-nitropyridine derivatives exhibited ether cleavage reaction on treatment with alcohols/amines in presence of base like K₂CO₃, Cs₂CO₃, NaOH, t-BuOK, etc. under microwave irradiation to yield corresponding phenols and 5-nitro-2-substituted pyridine.

References

Oussaid A., Thach L.N., Loupy A., Selective Dealkylation of Aryl Ether in Heterogeneous Basic Media under Microwave Irradiation, Tetrahedron Letters, 38, 2451-2454 (1997)
Sala T., Sargent M.V., Depsidone synthesis. Part 14, The total synthesis of psoromic acid: isopropyl ethers as useful phenolic protective groups, J Chem. Soc. Perkin Trans 1, 2593-2598 (1979)
Tiecco M., Selective Dealkylations of Aryl Alkyl Ethers, Thioethers, and Selenoethers, Synthesis, 749-759 (1988)
Lu Fachuang, Ralph John, DFRC Method for Lignin Analysis. 1. New Method for -Aryl Ether Cleavage: Lignin Model Studies, J. Agric. Food. Chem., 45, 4655-4660 (1997)
McOmie J.F.W., Watta M.L. and West D.E., Demethylation of aryl methyl ethers by boron tribromide,Tetrahedron, 24, 2289-2292 (1968)
Marion F., Williums D.E., Patrick B.O., Hollander I, Mallon R., Kim S.C., Roll D.M., Feldberg L., Soest R.V., Andersen R J.,Liphagal- a Selective Inhibitor of PI3 Kinase Isolated from the Sponge Aka coralliphaga: Structure Elucidation and Biomimetic Synthesis, Organic Letters, 321-324 (2006)
Kuhnert N., Clifford M.N., Radenac A.G., Boron trifluoride–etherate mediated synthesis of 3-desoxyanthocyanidins including a total synthesis of tricetanidin from black tea, Tetrahedron Letters, 42, 9261-9263 (2001)
Desai H.K., Joshi B.S., Pelletier W., Newton M.G., Crystal and molecular structure of 16,18-di-O-acetyl-16, 18-didemethyldelphinine, J Crystallographic and Spectroscopic Research,22, 375 (1992)
M. Hurriayoun Akhtar, S. Mahadevan, Faye Russell., Cleavage of 3-phenoxybenzoic acid by chicken microsomal preparations, Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes, 28, 527-543, (1993)
Walter Yu, Jeffrey M. Dener,Daniel A. Dickman, Paul Grothaus, Yun Ling, Liang Liu, Chris Havel, Kimberly Malesky, Tania Mahajan, Colin O’Brian, Emma J. Shelton, David Sperandio, Zhiwei Tong, Robert Yee and Joyce J. Mordenti., Identification of metabolites of the tryptase inhibitor CRA-9249: Observation of a metabolite derived from an unexpected hydroxylation pathwayBioorganic & Medicinal Chemistry Letters16, 4053-4058 (2006)
Bhatt M.V., Kulkarni S.U., Cleavage of Ethers, Synthesis, 249-282, (1983)
Burwell R.L. Jr., The Cleavage of Ethers, Chemical Review, 54, 615 (1954)
John T. Gupton., Topics in Heterocyclic Chemistry - Springer-Verlag Berlin Heidelberg , 53–92 (2006)
Sharghi H., Tamaddon F.,BeCl2 as a new highly selective reagent for dealkylation of aryl-methyl ethers, Tetrahedron52, 13623 (1996)
Urich D., Baerbel F., Herbert R., Gerhard S., Rainer Formaldehyd-O-oxid und Colchicine: ein eleganter Zugang zu Allocolchicinen, J. Prakt. Chem.,340, 468-471 (1998)
Radhakrishna A.S., Prasad K.R.K., Suri S.K., Sivaprakash K., Sing B.B., Potassium Fluoride on Alumina—A New Reagent for Selective-O-Demethylation of Arylalkyl Ethers, Synth. Commun, 21, 379 (1991)
Sato N., Kato Y.,Studies on pyrazines, A. convenient synthesis of 2, 5-dihydroxypyrazines, J. Herocycl. Chem., 23, 1677 (1986)
Siskin M., Katritzky Alan-R., Aqueous organic chemistry-Cleavage of diaryl ethers, Energy Fuels, 770-771 (1991)
Park Hyun-Ja, Lee Jong-Cheol, Kim Yeong-Joon, Lee Kee., Unexpected Behavior of 5-Phenoxypyrazole Derivatives, Bull. Korean. Chem. Soc26, 668-670 (2005)
Lidstrom P., Tierney J., Wathey B., Westman J., Corrigendum to “Microwave assisted organic synthesis—a review, Tetrahedron 57, 9225-9283 (2001)
Kappe C.O., Controlled Microwave Heating in Modern Organic Synthesis, Angew. Chem. Ind., 43, 6250 (2004)
Selvakumar S., Easwaramurthy M., Raju G.J., Ecofriendly solvent free microwave enhanced alkyl migration in N-alkyl aniline in dry media condition,Indian Journal of Chemistry, 46B, 713-715 (2007)
Deka N., Mariotte A.M., Boumendjel A.,Microwave mediated solvent-free acetylation of deactivated and hindered phenols, Green Chemistry, 263-264 (2001)
Fredrikson Anna, Elander S-Stone., Rapid microwave-assisted cleavage of methyl phenyl ethers: new method for synthesizing desmethyl precursors and for removing protecting groups, J. Label. Compd. Radiopharm., 45, 529-538 (2002)
Kulkarni P.P., Kadam A.J., Mane R.B., Desai U.V., Wadgaokar P.P., Demethylation of Methyl Aryl Ethers using Pyridine Hydrochloride in Solvent-free Conditions under Microwave Irradiation, J. Chem. Res (s), 39, 394-395 (1999)
Radhakrishna A.S., Prasad R.K.R., Rapid microwave-assisted cleavage of methyl phenyl ethers-new method for synthesizing desmethyl precursors and for removing protecting groups, Synth Commun, 21, 379-383 (1991)
Zhuan Fang, Guo-Chuan Zhou, Shi-Long Zheng, Guang-Li He, Ju-Lian Li, Ling He, Di BeiLithium chloride-catalyzed selective demethylation of aryl methyl ethers under microwave irradiation, Journal of Molecular Catalysis A: Chemical, 274, 16-23 (2007)

[ref1] Oussaid A., Thach L.N., Loupy A., Selective Dealkylation of Aryl Ether in Heterogeneous Basic Media under Microwave Irradiation, Tetrahedron Letters, 38, 2451-2454 (1997)

[ref2] Sala T., Sargent M.V., Depsidone synthesis. Part 14, The total synthesis of psoromic acid: isopropyl ethers as useful phenolic protective groups, J Chem. Soc. Perkin Trans 1, 2593-2598 (1979)

[ref3] Tiecco M., Selective Dealkylations of Aryl Alkyl Ethers, Thioethers, and Selenoethers, Synthesis, 749-759 (1988)

[ref4] Lu Fachuang, Ralph John, DFRC Method for Lignin Analysis. 1. New Method for -Aryl Ether Cleavage: Lignin Model Studies, J. Agric. Food. Chem., 45, 4655-4660 (1997)

[ref5] McOmie J.F.W., Watta M.L. and West D.E., Demethylation of aryl methyl ethers by boron tribromide,Tetrahedron, 24, 2289-2292 (1968)

[ref6] Marion F., Williums D.E., Patrick B.O., Hollander I, Mallon R., Kim S.C., Roll D.M., Feldberg L., Soest R.V., Andersen R J.,Liphagal- a Selective Inhibitor of PI3 Kinase Isolated from the Sponge Aka coralliphaga: Structure Elucidation and Biomimetic Synthesis, Organic Letters, 321-324 (2006)

[ref7] Kuhnert N., Clifford M.N., Radenac A.G., Boron trifluoride–etherate mediated synthesis of 3-desoxyanthocyanidins including a total synthesis of tricetanidin from black tea, Tetrahedron Letters, 42, 9261-9263 (2001)

[ref8] Desai H.K., Joshi B.S., Pelletier W., Newton M.G., Crystal and molecular structure of 16,18-di-O-acetyl-16, 18-didemethyldelphinine, J Crystallographic and Spectroscopic Research,22, 375 (1992)

[ref9] M. Hurriayoun Akhtar, S. Mahadevan, Faye Russell., Cleavage of 3-phenoxybenzoic acid by chicken microsomal preparations, Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes, 28, 527-543, (1993)

[ref10] Walter Yu, Jeffrey M. Dener,Daniel A. Dickman, Paul Grothaus, Yun Ling, Liang Liu, Chris Havel, Kimberly Malesky, Tania Mahajan, Colin O’Brian, Emma J. Shelton, David Sperandio, Zhiwei Tong, Robert Yee and Joyce J. Mordenti., Identification of metabolites of the tryptase inhibitor CRA-9249: Observation of a metabolite derived from an unexpected hydroxylation pathwayBioorganic & Medicinal Chemistry Letters16, 4053-4058 (2006)

[ref11] Bhatt M.V., Kulkarni S.U., Cleavage of Ethers, Synthesis, 249-282, (1983)

[ref12] Burwell R.L. Jr., The Cleavage of Ethers, Chemical Review, 54, 615 (1954)

[ref13] John T. Gupton., Topics in Heterocyclic Chemistry - Springer-Verlag Berlin Heidelberg , 53–92 (2006)

[ref14] Sharghi H., Tamaddon F.,BeCl2 as a new highly selective reagent for dealkylation of aryl-methyl ethers, Tetrahedron52, 13623 (1996)

[ref15] Urich D., Baerbel F., Herbert R., Gerhard S., Rainer Formaldehyd-O-oxid und Colchicine: ein eleganter Zugang zu Allocolchicinen, J. Prakt. Chem.,340, 468-471 (1998)

[ref16] Radhakrishna A.S., Prasad K.R.K., Suri S.K., Sivaprakash K., Sing B.B., Potassium Fluoride on Alumina—A New Reagent for Selective-O-Demethylation of Arylalkyl Ethers, Synth. Commun, 21, 379 (1991)

[ref17] Sato N., Kato Y.,Studies on pyrazines, A. convenient synthesis of 2, 5-dihydroxypyrazines, J. Herocycl. Chem., 23, 1677 (1986)

[ref18] Siskin M., Katritzky Alan-R., Aqueous organic chemistry-Cleavage of diaryl ethers, Energy Fuels, 770-771 (1991)

[ref19] Park Hyun-Ja, Lee Jong-Cheol, Kim Yeong-Joon, Lee Kee., Unexpected Behavior of 5-Phenoxypyrazole Derivatives, Bull. Korean. Chem. Soc26, 668-670 (2005)

[ref20] Lidstrom P., Tierney J., Wathey B., Westman J., Corrigendum to “Microwave assisted organic synthesis—a review, Tetrahedron 57, 9225-9283 (2001)

[ref21] Kappe C.O., Controlled Microwave Heating in Modern Organic Synthesis, Angew. Chem. Ind., 43, 6250 (2004)

[ref22] Selvakumar S., Easwaramurthy M., Raju G.J., Ecofriendly solvent free microwave enhanced alkyl migration in N-alkyl aniline in dry media condition,Indian Journal of Chemistry, 46B, 713-715 (2007)

[ref23] Deka N., Mariotte A.M., Boumendjel A.,Microwave mediated solvent-free acetylation of deactivated and hindered phenols, Green Chemistry, 263-264 (2001)

[ref24] Fredrikson Anna, Elander S-Stone., Rapid microwave-assisted cleavage of methyl phenyl ethers: new method for synthesizing desmethyl precursors and for removing protecting groups, J. Label. Compd. Radiopharm., 45, 529-538 (2002)

[ref25] Kulkarni P.P., Kadam A.J., Mane R.B., Desai U.V., Wadgaokar P.P., Demethylation of Methyl Aryl Ethers using Pyridine Hydrochloride in Solvent-free Conditions under Microwave Irradiation, J. Chem. Res (s), 39, 394-395 (1999)

[ref26] Radhakrishna A.S., Prasad R.K.R., Rapid microwave-assisted cleavage of methyl phenyl ethers-new method for synthesizing desmethyl precursors and for removing protecting groups, Synth Commun, 21, 379-383 (1991)

[ref27] Zhuan Fang, Guo-Chuan Zhou, Shi-Long Zheng, Guang-Li He, Ju-Lian Li, Ling He, Di BeiLithium chloride-catalyzed selective demethylation of aryl methyl ethers under microwave irradiation, Journal of Molecular Catalysis A: Chemical, 274, 16-23 (2007)