Synthesis of 4-hydroxy-1-methyl-4-(2-furyl)-3-(2- furylhydroxymethyl) piperidine and Transformation into perhydro[1,3,2]dioxaborinino[5,4-c]pyridine
Main Article Content
Abstract
Having been synthesized successfully heterocyclic system, namely 2-aryl-N-methyl-4,8a-di(α-furyl)perhydro[1,2,3]dioxaborinino-[5,4-c]pyridine contains two piperidine and dioxaborinine rings. This new heterocyclic system was prepared from the reaction of N-methyl-3-(α-hydroxyfuryl)-4-(α-furyl)-γ-piperidol and some derivatives of arylboronic acid. The structure of new substances was confirmed by physical-chemical method including 1Н NMR, IR, MS. Futhermore, PASS online Program investigated that di(α-furyl)perhydro[1,2,3]dioxaborinino-[5,4-c]pyridine derivatives have high potential of bioactivities such as dermatology, spasmology, anticoagulant and antipsoriatic agent … which promote us to develop the new method affording this kind of compounds.
Keywords:
piperidine, dioxaborinine, Mannich reaction, multicomponent condensation reaction, azacrown ether
References
[1] Soldatenkov A.T., Kolyadina N.M., Shendrik I.V., “Base of Organic Chemistry of Drug”, Hanoi, Vietnam – 2010. (original in Vietnamese: “Cơ sở hóa học hữu cơ của thuốc hóa dược”).
[2] Soldatenkov A.T., Kolyadina N.M., Le Tuan Anh. “Application of Organic Chemistry: Pesticides and growth regulators”, Moscow. Russia – 2010 (original in Russian: “Прикладная органическая химия. Пестициды и регуляторы роста”).
[3] Soldatenkov A.T., Le Tuan Anh, Kolyadina N.M., Ylin A.P., Truong Hong Hieu, “Drugs. Application of fine organic synthesis”, Hanoi, Vietnam – 2014. (original in Russian: “Лекарства. Прикладной тонкий органический синтез”).
[4] Soldatenkov A.T., Le Tuan Anh, F.I. Zubkov, Luu Van Boi, Truong Hong Hieu, K.B. Polianskyi. “Stereochemical application of bioactive compounds”, Hanoi, Vietnam – 2015. (original in Russian “Прикладная стереохимия биологически активных веществ”).
[5] Amitabh Jha, Katherine M. Duffield, Matthew R. Ness, Sujatha Ravoori, Gabrielle Andrews, Khushwant S. Bhullar, H.P. Vasantha Rupasinghe, Jan Balzarini. Curcumin-inspired cytotoxic 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones: A novel group of topoisomerase II alpha inhibitors. Bioorganic & Medicinal Chemistry, 23 (19), (2015), 640.
[6] Umashankar Das, Swagatika Das, Brian Bandy, James P. Stables, Jonathan R. Dimmock. N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents. Bioorganic & Medicinal Chemistry, 16 (7), (2008) 3602.
[7] Chyong Khong Khieu, A. T. Soldatenkov, Le Tuan Anh, A. N. Levov, A. F Smol’yakov, V. N. Khrustalev and M. Yu. Antipin. “Synthesis and molecular structures of dibenzo(perhydrotriazino)aza-14-crown-4 ethers”. Russian Journal of Organic Chemistry, Vol. 47, No. 5, (2011) 766.
[8] Truong Hong Hieu, A. T. Soldatenkov, Le Tuan Anh, To Hai Tung and S. A. Soldatova. “Domino synthesis of the first representative of a dibenzo(perhydropyrimidino)aza-14-crown-4 ethers series”. Chemistry of Heterocyclic Compounds, Vol. 47, No. 10, January, (2012) 1315.
[9] A. T. Le, H. H. Truong, P. T. T. Nguyen, N. D. Thi, H. T. To, H. P. Thi and A. T. Soldatenkov, Mendeleev Communications, 25 (2015) 224.
[10] Le Tuan Anh, K. B. Polyanskiy, J. A. Mamyrbekova, A. T. Soldatenkov, S. A. Soldatova, V. V. Kurilkin, and P. B. Terentiev. Synthesis and spectral characteristics of 2-aryl-6-methyl- and 2-aryl-6-benzyl-4,8a-diphenylperhydro[1,2,3]dioxaborinino[5,4-c]pyridines. Chemistry of Heterocyclic Compounds. 44(8), (2008) 1009.
[11] Le Tuan Anh, A. T. Soldatenkov, J. A. Mamyrbekova, S. A. Soldatova, K. B. Polyanskiy, Tran Thanh Tung, V. N. Khrustalev. Synthesis and molecular structure of substituted 2-hydr-oxyperhydro[1,3,2]dioxaborinino[5,4-c]pyridines, perhydro-[1,3]dioxano[5,4-c]pyridine, and their precursor 4-hydroxy-1-methyl-4-phenyl-3-(phenylhydroxymethyl)piperidine. Chemistry of Heterocyclic Compounds. 44(11), (2008) 1404.
[12] Le Tuan Anh, A.T. Soldatenkov, Truong Hong Hieu, S.A.Soldatova, A.N. Levov, K.B. Polyanskiy. Synthesis of derivatives of pyrido-[1,2-c][1,3,2]-oxazaborinine and pyrido-[2,1,6-f,g][1,3,7,2] dioxazaphosphacyclodecane. Chemistry of Heterocyclic Compounds, 44 (12), (2008) 1527.
[13] S. K. Gurung, S. Thapa, A. Kafle, D. A. Dickie, R. Giri. Copper-Catalyzed Suzuki-Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates. Org. Lett., 16, (2014), 1264-1267.
[14] P. Leowanawat, N. Zhang, A.-M. Remerita, B. M. Rosen, V. Percec. Ni(COD)2/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature. J. Org. Chem., 76, (2011), 9946-9955.
[15] Filimonov D.A., Lagunin A.A., Gloriozova T.A., Rudik A.V., Druzhilovskii D.S., Pogodin P.V., Poroikov V.V. Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chemistry of Heterocyclic Compounds, 50 (3), (2014), 444-457.
[2] Soldatenkov A.T., Kolyadina N.M., Le Tuan Anh. “Application of Organic Chemistry: Pesticides and growth regulators”, Moscow. Russia – 2010 (original in Russian: “Прикладная органическая химия. Пестициды и регуляторы роста”).
[3] Soldatenkov A.T., Le Tuan Anh, Kolyadina N.M., Ylin A.P., Truong Hong Hieu, “Drugs. Application of fine organic synthesis”, Hanoi, Vietnam – 2014. (original in Russian: “Лекарства. Прикладной тонкий органический синтез”).
[4] Soldatenkov A.T., Le Tuan Anh, F.I. Zubkov, Luu Van Boi, Truong Hong Hieu, K.B. Polianskyi. “Stereochemical application of bioactive compounds”, Hanoi, Vietnam – 2015. (original in Russian “Прикладная стереохимия биологически активных веществ”).
[5] Amitabh Jha, Katherine M. Duffield, Matthew R. Ness, Sujatha Ravoori, Gabrielle Andrews, Khushwant S. Bhullar, H.P. Vasantha Rupasinghe, Jan Balzarini. Curcumin-inspired cytotoxic 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones: A novel group of topoisomerase II alpha inhibitors. Bioorganic & Medicinal Chemistry, 23 (19), (2015), 640.
[6] Umashankar Das, Swagatika Das, Brian Bandy, James P. Stables, Jonathan R. Dimmock. N-Aroyl-3,5-bis(benzylidene)-4-piperidones: A novel class of antimycobacterial agents. Bioorganic & Medicinal Chemistry, 16 (7), (2008) 3602.
[7] Chyong Khong Khieu, A. T. Soldatenkov, Le Tuan Anh, A. N. Levov, A. F Smol’yakov, V. N. Khrustalev and M. Yu. Antipin. “Synthesis and molecular structures of dibenzo(perhydrotriazino)aza-14-crown-4 ethers”. Russian Journal of Organic Chemistry, Vol. 47, No. 5, (2011) 766.
[8] Truong Hong Hieu, A. T. Soldatenkov, Le Tuan Anh, To Hai Tung and S. A. Soldatova. “Domino synthesis of the first representative of a dibenzo(perhydropyrimidino)aza-14-crown-4 ethers series”. Chemistry of Heterocyclic Compounds, Vol. 47, No. 10, January, (2012) 1315.
[9] A. T. Le, H. H. Truong, P. T. T. Nguyen, N. D. Thi, H. T. To, H. P. Thi and A. T. Soldatenkov, Mendeleev Communications, 25 (2015) 224.
[10] Le Tuan Anh, K. B. Polyanskiy, J. A. Mamyrbekova, A. T. Soldatenkov, S. A. Soldatova, V. V. Kurilkin, and P. B. Terentiev. Synthesis and spectral characteristics of 2-aryl-6-methyl- and 2-aryl-6-benzyl-4,8a-diphenylperhydro[1,2,3]dioxaborinino[5,4-c]pyridines. Chemistry of Heterocyclic Compounds. 44(8), (2008) 1009.
[11] Le Tuan Anh, A. T. Soldatenkov, J. A. Mamyrbekova, S. A. Soldatova, K. B. Polyanskiy, Tran Thanh Tung, V. N. Khrustalev. Synthesis and molecular structure of substituted 2-hydr-oxyperhydro[1,3,2]dioxaborinino[5,4-c]pyridines, perhydro-[1,3]dioxano[5,4-c]pyridine, and their precursor 4-hydroxy-1-methyl-4-phenyl-3-(phenylhydroxymethyl)piperidine. Chemistry of Heterocyclic Compounds. 44(11), (2008) 1404.
[12] Le Tuan Anh, A.T. Soldatenkov, Truong Hong Hieu, S.A.Soldatova, A.N. Levov, K.B. Polyanskiy. Synthesis of derivatives of pyrido-[1,2-c][1,3,2]-oxazaborinine and pyrido-[2,1,6-f,g][1,3,7,2] dioxazaphosphacyclodecane. Chemistry of Heterocyclic Compounds, 44 (12), (2008) 1527.
[13] S. K. Gurung, S. Thapa, A. Kafle, D. A. Dickie, R. Giri. Copper-Catalyzed Suzuki-Miyaura Coupling of Arylboronate Esters: Transmetalation with (PN)CuF and Identification of Intermediates. Org. Lett., 16, (2014), 1264-1267.
[14] P. Leowanawat, N. Zhang, A.-M. Remerita, B. M. Rosen, V. Percec. Ni(COD)2/PCy3 Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature. J. Org. Chem., 76, (2011), 9946-9955.
[15] Filimonov D.A., Lagunin A.A., Gloriozova T.A., Rudik A.V., Druzhilovskii D.S., Pogodin P.V., Poroikov V.V. Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chemistry of Heterocyclic Compounds, 50 (3), (2014), 444-457.