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3,4-Dietilpirolün Sentezi ve Karakterizasyonu

Year 2006, Volume: 10 Issue: 1, 21 - 24, 10.04.2009

Abstract

Pirol ve türevleri organik ve biyokimyada önemli heterosiklik bileşiklerdir ve birçok doğal üründe bulunmaktadırlar. Bu çalışmada, porfirin vb. gibi doğal ürünlerin sentezinde kullanılabilecek bir bileşik olan 3,4-dietilpirolün sentezi gerçekleştirilmiştir. Bu amaç için ilk önce bir α-halojenleme reaksiyonu ile bütanalden 2-bromobütanal elde edilmiş ve yine bütanal, morfolin ile etkileştirilerek 1-morfolino-1-büten enamini sentezlenmiştir. 2-Bromobutanal ve 1-morfolino-1-büten uygun şartlarda etkileştirilerek 2,3-dietilsüksinaldehit elde edilmiştir. 2,3-Dietilsüksinaldehitin amonyum karbonat ile reaksiyonu sonucu 3,4-dietilpirol sentezlenmiştir.

References

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  • A.S. Demir, İ.M. Akhmedov and Ö. Şeşenoğlu, “Synthesis of 1,2,3,5-Tetrasubstituted Pyrrole Derivatives from 2-(2-Bromoallyl)-1,3-dicarbonyl Compounds”, Tetrahedron, 58, (2002), 9793–9799.
  • S.H. Hwang, M.J. Kurth, “1,3-Dipolar Cycloaddition of Nitrile Oxides to 1-Phenylsulfonyl-1,3-butadienes: Synthesis of 3-(4,5-Dihydroisoxazol-5-yl)pyrroles”, Tetrahedron Letters, 43, (2002), 53–56.
  • C.E. Hewton, M.C. Kimber and D.K. Taylor, “A One-pot Synthesis of Thiophene and Pyrrole Derivatives from Readily Accessible 3,5-Dihydro- ,2-dioxines”, Tetrahedron Letters, 43, (2002), 3199–
  • P.M.T. Ferreira, H.L.S. Maia and L.S. Monteiro, “Synthesis of 2,3,5-Substituted Pyrrole Derivatives”, Tetrahedron Letters, 43, (2002), 4495–4497.
  • X. Fanand, Y. Zhang, “SmI2-mediated Synthesis of ,4-Diarylpyrroles from Phenacyl Azides”, Tetrahedron Letters, 43, (2002), 1863–1865.
  • M.K. Jeon, K. Kim, “Synthesis of 3-(Alkylamino and anilino)-4-benzyloxycarbonyl-1H-pyrrole-2,5-diones via 5-[(Alkylamino and anilino)(cyano)]-2,2- dimethyl-1,3-dioxane-4,6-diones”, Letters, 43, (2002), 3415–3418. Tetrahedron
  • A.V. Kel’in, A.W. Sromek, and V. Gevorgyan, “A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines: Efficient Synthesis of Pyrroles and Pyrrole- Containing Heterocycles”, J. Am. Chem. Soc., 123, (2001), 2074-2075.
  • B.C. Ranu, A. Hajra, “Synthesis of Alkyl-substituted Pyrroles by Three-component Coupling of Carbonyl Compound, Amine and Nitro-alkane/alkene on a Solid Surface of Silica gel/alumina Under Micrawave Irradiation”, Tetrahedron, 57, (2001), 4767-4773.
  • R.J. Andrew and J.M. Mellor, “Synthesis of Trifluoromethylpyrroles and Related Heterocycles from 4-Ethyloxy-1,1,1-trifluorobut-3-ene-2-one”, Tetrahedron, 56, (2000), 7267–7272.
  • B. Quiclet-Sire, I. Thevenot and S.Z. Zard, “A New and Practical Synthesis of Pyrroles” Tetrahedron Letters, 36, (1995), 9469-9470.
  • A. W.Trautwein, R.D.Süβmuth and G. Jung, “Hantzsch Pyrrole Synthesis On Solid Support”, Bioorganic & Medicinal Chemistry Letters , 8, (1998), 2381-2384.
  • J.L. Wang, C.H. Ueng and M.C.P. Yeh, “Synthesis of Pyrrole Derivatives Mediated by Dicobalthexacarbonyl”, Tetrahedron Letters, 36, (1995), 2823-2826.
  • A.M.M Mjalli, S. Sarshar and T.J. Baiga, “Solid Phase Synthesis of Pyrroles Derived from a Four Component Condensation”, Tetrahedron Letters, 37, (1996), 2943-2946.
  • S. Kumar, V. Kumar and S.S. Chimni, “Novel Indium-mediated Ternary Reactions Between Indole- carboxaldehydes–allyl Bromide–enamines: Facile Synthesis of Bisindolyl- and Indolyl-heterocyclic Alkanes”, Tetrahedron Letters, 44, (2003), 2101–
  • M. Yasuda, J. Morimoto, I. Shibata, and A. Baba, “Organotin(IV) Enamines as Selective Reagents: Coupling with α-Halocarbonyls for Synthesis of Substituted Pyrroles”, Tetrahedron Letters, 38, (1997), 3265-3266.
  • Y. Aoyogi, T. Mizusaki, and A. Ohta, “Facile and Efficient Synthesis of Pyrroles and Indoles via Palladium-Catalyzed Oxidation of Hydroxy- Enamines and –Amines” Tetrahedron Letters, 37, (1996), 9203-9206.
  • M. Graça, H. Vicente and K.M. Smith, “Porphyrins and Derivatives: Synthetic Strategies and Reactivity Profiles”, Current Organic Chemistry, 4, (2000), 139-174.
  • J. Tang, J.G. Verkade, “Nonionic Superbase- Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and alpha.-C-Acyl Amino Acid Esters”, J. Org. Chem., 59, (1994), 7793-7802.
  • D.H.R. Barton, S.Z. Zard,” A New Synthesis of Pyrroles from Nitroalkenes”, J. Chem. Soc., Chem. Commun. 1985, 1098.
  • J.L. Sessler, A. Mozaffari and M.R. Johnson, “3,4-Diethylpyrrole Octaethylporphyrin”, Organic Syntheses, 70, (1991), 77. and 2,3,7,8,12,13,17,18
  • J.G. Lee, I.S. Park and J.W. Seo, “Halogenation of Aldehydes and Ketones by Selenium (IV) Oxyhalides Generated in-situ from Selenium Dioxide and Halotrimethylsilanes”, Bull. Korean Chem. Soc., 16, (1995), 349-355.
  • J. Yu, “Synthesis and Mechanistic Studies on the Monoamine Oxidase (MAO) Catalyzed Oxidation of ,4-Disubstituted-1,2,3,6-Tetrahydropyridines”, Doctorate Thesis, (1998). C. Paal, Ber., 18, (1885), 367. L. Knorr, Ber., 18, (1885), 299.
  • H.S.P. Rao and S. Jothilingam, “One-pot Synthesis of Pyrrole Derivatives from (E)-1,4-Diaryl- butene-1,4-diones”, (2001), 6595–6597.
  • Tetrahedron Letters, 42, C.W. Ong, C.M. Chen, L.H. Wang and J.J. Jan, “Efficient Synthesis of Pyrroles from Chemoselective Addition of Primary Amines to 1,6-Dioxo-2,4- dienes”, J. Org. Chem., 63, (1998), 9131-9134.
  • P.E. Just, K.I. Chane-Ching and P.C. Lacaze, “Synthesis of 2,5-di(2-thienyl)-1H-pyrrole N-linked with conjugated bridges”, Tetrahedron, 58, (2002), 3472.
  • B. Chandrasekhar, S. R. Ramadas and D. V. Ramana, “A Convenient and Simple Method for the Synthesis of Condensed γ-Lactams and Substituted Xanthones from Cyclic-1,3-diketones”, Tetrahedron, , (2000), 5947-5952.
  • R.A. Gadzhili, R.A. Nadzhafova and Ö. Şeşenoğlu, Alkoxycarbonyl-Methyl-2-Alkylpyrroles from Dichloro- and Methoxychloropropylalkyl Ketones”, Turk J Chem, 26, (2002), 379-383. of
Year 2006, Volume: 10 Issue: 1, 21 - 24, 10.04.2009

Abstract

References

  • A. Alberola, A.G. Ortega, M. L. Sidaba and C. Sanudo, “Versatility of Weinreb Amides in the Knorr Pyrrole Synthesis”, Tetrahedron, 55, (1999), 6566.
  • A.S. Demir, İ.M. Akhmedov and Ö. Şeşenoğlu, “Synthesis of 1,2,3,5-Tetrasubstituted Pyrrole Derivatives from 2-(2-Bromoallyl)-1,3-dicarbonyl Compounds”, Tetrahedron, 58, (2002), 9793–9799.
  • S.H. Hwang, M.J. Kurth, “1,3-Dipolar Cycloaddition of Nitrile Oxides to 1-Phenylsulfonyl-1,3-butadienes: Synthesis of 3-(4,5-Dihydroisoxazol-5-yl)pyrroles”, Tetrahedron Letters, 43, (2002), 53–56.
  • C.E. Hewton, M.C. Kimber and D.K. Taylor, “A One-pot Synthesis of Thiophene and Pyrrole Derivatives from Readily Accessible 3,5-Dihydro- ,2-dioxines”, Tetrahedron Letters, 43, (2002), 3199–
  • P.M.T. Ferreira, H.L.S. Maia and L.S. Monteiro, “Synthesis of 2,3,5-Substituted Pyrrole Derivatives”, Tetrahedron Letters, 43, (2002), 4495–4497.
  • X. Fanand, Y. Zhang, “SmI2-mediated Synthesis of ,4-Diarylpyrroles from Phenacyl Azides”, Tetrahedron Letters, 43, (2002), 1863–1865.
  • M.K. Jeon, K. Kim, “Synthesis of 3-(Alkylamino and anilino)-4-benzyloxycarbonyl-1H-pyrrole-2,5-diones via 5-[(Alkylamino and anilino)(cyano)]-2,2- dimethyl-1,3-dioxane-4,6-diones”, Letters, 43, (2002), 3415–3418. Tetrahedron
  • A.V. Kel’in, A.W. Sromek, and V. Gevorgyan, “A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines: Efficient Synthesis of Pyrroles and Pyrrole- Containing Heterocycles”, J. Am. Chem. Soc., 123, (2001), 2074-2075.
  • B.C. Ranu, A. Hajra, “Synthesis of Alkyl-substituted Pyrroles by Three-component Coupling of Carbonyl Compound, Amine and Nitro-alkane/alkene on a Solid Surface of Silica gel/alumina Under Micrawave Irradiation”, Tetrahedron, 57, (2001), 4767-4773.
  • R.J. Andrew and J.M. Mellor, “Synthesis of Trifluoromethylpyrroles and Related Heterocycles from 4-Ethyloxy-1,1,1-trifluorobut-3-ene-2-one”, Tetrahedron, 56, (2000), 7267–7272.
  • B. Quiclet-Sire, I. Thevenot and S.Z. Zard, “A New and Practical Synthesis of Pyrroles” Tetrahedron Letters, 36, (1995), 9469-9470.
  • A. W.Trautwein, R.D.Süβmuth and G. Jung, “Hantzsch Pyrrole Synthesis On Solid Support”, Bioorganic & Medicinal Chemistry Letters , 8, (1998), 2381-2384.
  • J.L. Wang, C.H. Ueng and M.C.P. Yeh, “Synthesis of Pyrrole Derivatives Mediated by Dicobalthexacarbonyl”, Tetrahedron Letters, 36, (1995), 2823-2826.
  • A.M.M Mjalli, S. Sarshar and T.J. Baiga, “Solid Phase Synthesis of Pyrroles Derived from a Four Component Condensation”, Tetrahedron Letters, 37, (1996), 2943-2946.
  • S. Kumar, V. Kumar and S.S. Chimni, “Novel Indium-mediated Ternary Reactions Between Indole- carboxaldehydes–allyl Bromide–enamines: Facile Synthesis of Bisindolyl- and Indolyl-heterocyclic Alkanes”, Tetrahedron Letters, 44, (2003), 2101–
  • M. Yasuda, J. Morimoto, I. Shibata, and A. Baba, “Organotin(IV) Enamines as Selective Reagents: Coupling with α-Halocarbonyls for Synthesis of Substituted Pyrroles”, Tetrahedron Letters, 38, (1997), 3265-3266.
  • Y. Aoyogi, T. Mizusaki, and A. Ohta, “Facile and Efficient Synthesis of Pyrroles and Indoles via Palladium-Catalyzed Oxidation of Hydroxy- Enamines and –Amines” Tetrahedron Letters, 37, (1996), 9203-9206.
  • M. Graça, H. Vicente and K.M. Smith, “Porphyrins and Derivatives: Synthetic Strategies and Reactivity Profiles”, Current Organic Chemistry, 4, (2000), 139-174.
  • J. Tang, J.G. Verkade, “Nonionic Superbase- Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and alpha.-C-Acyl Amino Acid Esters”, J. Org. Chem., 59, (1994), 7793-7802.
  • D.H.R. Barton, S.Z. Zard,” A New Synthesis of Pyrroles from Nitroalkenes”, J. Chem. Soc., Chem. Commun. 1985, 1098.
  • J.L. Sessler, A. Mozaffari and M.R. Johnson, “3,4-Diethylpyrrole Octaethylporphyrin”, Organic Syntheses, 70, (1991), 77. and 2,3,7,8,12,13,17,18
  • J.G. Lee, I.S. Park and J.W. Seo, “Halogenation of Aldehydes and Ketones by Selenium (IV) Oxyhalides Generated in-situ from Selenium Dioxide and Halotrimethylsilanes”, Bull. Korean Chem. Soc., 16, (1995), 349-355.
  • J. Yu, “Synthesis and Mechanistic Studies on the Monoamine Oxidase (MAO) Catalyzed Oxidation of ,4-Disubstituted-1,2,3,6-Tetrahydropyridines”, Doctorate Thesis, (1998). C. Paal, Ber., 18, (1885), 367. L. Knorr, Ber., 18, (1885), 299.
  • H.S.P. Rao and S. Jothilingam, “One-pot Synthesis of Pyrrole Derivatives from (E)-1,4-Diaryl- butene-1,4-diones”, (2001), 6595–6597.
  • Tetrahedron Letters, 42, C.W. Ong, C.M. Chen, L.H. Wang and J.J. Jan, “Efficient Synthesis of Pyrroles from Chemoselective Addition of Primary Amines to 1,6-Dioxo-2,4- dienes”, J. Org. Chem., 63, (1998), 9131-9134.
  • P.E. Just, K.I. Chane-Ching and P.C. Lacaze, “Synthesis of 2,5-di(2-thienyl)-1H-pyrrole N-linked with conjugated bridges”, Tetrahedron, 58, (2002), 3472.
  • B. Chandrasekhar, S. R. Ramadas and D. V. Ramana, “A Convenient and Simple Method for the Synthesis of Condensed γ-Lactams and Substituted Xanthones from Cyclic-1,3-diketones”, Tetrahedron, , (2000), 5947-5952.
  • R.A. Gadzhili, R.A. Nadzhafova and Ö. Şeşenoğlu, Alkoxycarbonyl-Methyl-2-Alkylpyrroles from Dichloro- and Methoxychloropropylalkyl Ketones”, Turk J Chem, 26, (2002), 379-383. of
There are 28 citations in total.

Details

Primary Language English
Journal Section TEMEL BİLİMLER
Authors

B. Dede This is me

A. Gülce This is me

Publication Date April 10, 2009
Published in Issue Year 2006 Volume: 10 Issue: 1

Cite

APA Dede, B., & Gülce, A. (2009). 3,4-Dietilpirolün Sentezi ve Karakterizasyonu. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 10(1), 21-24. https://doi.org/10.19113/sdufbed.43699
AMA Dede B, Gülce A. 3,4-Dietilpirolün Sentezi ve Karakterizasyonu. J. Nat. Appl. Sci. April 2009;10(1):21-24. doi:10.19113/sdufbed.43699
Chicago Dede, B., and A. Gülce. “3,4-Dietilpirolün Sentezi Ve Karakterizasyonu”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 10, no. 1 (April 2009): 21-24. https://doi.org/10.19113/sdufbed.43699.
EndNote Dede B, Gülce A (April 1, 2009) 3,4-Dietilpirolün Sentezi ve Karakterizasyonu. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 10 1 21–24.
IEEE B. Dede and A. Gülce, “3,4-Dietilpirolün Sentezi ve Karakterizasyonu”, J. Nat. Appl. Sci., vol. 10, no. 1, pp. 21–24, 2009, doi: 10.19113/sdufbed.43699.
ISNAD Dede, B. - Gülce, A. “3,4-Dietilpirolün Sentezi Ve Karakterizasyonu”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi 10/1 (April 2009), 21-24. https://doi.org/10.19113/sdufbed.43699.
JAMA Dede B, Gülce A. 3,4-Dietilpirolün Sentezi ve Karakterizasyonu. J. Nat. Appl. Sci. 2009;10:21–24.
MLA Dede, B. and A. Gülce. “3,4-Dietilpirolün Sentezi Ve Karakterizasyonu”. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, vol. 10, no. 1, 2009, pp. 21-24, doi:10.19113/sdufbed.43699.
Vancouver Dede B, Gülce A. 3,4-Dietilpirolün Sentezi ve Karakterizasyonu. J. Nat. Appl. Sci. 2009;10(1):21-4.

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