AN IMPORTANT FIVE-MEMBERED HETEROAROMATIC COMPOUND: PYRROLE

Year 2006, Volume: 22 Issue: 1, 121 - 141, 01.02.2006

Bülent Dede

Abstract

The synthesis of pyrroles is an important area of heterocyclic chemistry due primarily to the fact that many pyrroles are subunits of natural products. Several alkylpyrrole derivatives have also been shown to possess remarkable biological activity. Although there are a quite number of methods available for the synthesis of pyrroles, most of them involve multistep synthetic operations which lower the overall yield. Thus, development of new synthetic methods still remains an attractive goal. In this review, a short information is given about pyrrole and then it is investigated studies about synthesis of pyrroles those is made for last twenty years.

Keywords

Pyrrole, Pyrrole synthesis, Five-membered ring

ÖNEMLİ BİR BEŞ-ÜYELİ HETEROAROMATİK BİLEŞİK: PİROL

Abstract

Piroller, çoğu doğal ürünlerin özünü oluşturduğundan dolayı heterosiklik kimyada pirollerin sentezinin önemli bir yeri vardır. Çeşitli alkilpirol türevlerinin çok iyi bir derecede biyolojik aktiviteye sahip olduğu görülmüştür. Bundan dolayı pirollerin sentezi amacıyla kullanışlı birçok metot olmasına rağmen bu metotların birçoğu çok fazla sentetik basamak içerdiklerinden dolayı sonuçta oluşan pirol türevlerinin verimleri yeteri kadar yüksek olmamaktadır. Bundan dolayı pirol türevlerinin sentezi için yapılan çalışmalar halen yapılmaya devam etmektedir. Bu makalede pirol hakkında kısa bir bilgi verildikten sonra pirolün sentezi için son yirmi yıl içerisinde yapılan çalışmalar incelenmiştir.

Keywords

Pirol, Pirol sentezi, Beş-üyeli halka

References

• Ün, R., Halkalı Organik Bileşikler, s 287, İstanbul Üniversitesi Yayınları İstanbul, 1977.
• Trautwein, A.W., Jung, G., Solid-Phase Synthesis of Pyrrole From Enaminones and Nitroalkenes, Tetrahedron Letters, 39(45), 8263-8266, 1988.
• Rink, H., Solid-Phase Synthesis of Protected Peptide Fragments Using a Trialkoxy-Diphenyl-Methylester Resin, Tetrahedron Letters, 28(33), 3787-3790, 1987.
• Clemens, R.J., Hyatt, J.A., Acetoacetylation with 2,2,6-Trimethyl-4H-1,3-dioxin-4-one: A Convenient Alternative to Diketene, Journal of Organic Chemistry, 50, 2431, 1985.
• Mjalli, A.M.M., Sarshar, S., Baiga, T.J., Solid Phase Synthesis of Pyrroles Derived from a Four Component Condensation, Tetrahedron Letters, 37(17), 2943-2946, 1996.
• Trautwein, A.W., Süβmuth, R.D., Jung, G., Hantzsch Pyrrole Synthesis On Solid Support, Bioorganic & Medicinal Chemistry Letters, 8(17), 2381-2384, 1998.
• Barton, D.H.R., Kervagoret, J., Zard, S.Z., A Useful Synthesis of Pyrroles From Nitroolefins, Tetrahedron, 46(21), 7587-7598, 1990.
• Quiclet-Sire, B., Thévenot, I., Zard, S.Z., A New and Practical Synthesis of Pyrroles, Tetrahedron Letters, 36(52), 9469-9470, 1995.
• Fejes, I., Toke, L., Blasko, G., Nyerges, M., Pak, C.S., A New Synthesis of 3,5-Diaryl-pyrrole-2-carboxylic Acids and Esters, Tetrahedron, 56(43), 8545-8553, 2000.
• Wang, J.L., Ueng, C.H., Yeh, M.C.P., Synthesis of Pyrrole Derivatives Mediated by Dicobalthexacarbonyl, Tetrahedron Letters, 36(16), 2823-2826, 1995.
• Lockwood, R.F., Nicholas, K.M., Transition Metal-Stabilized Carbenium Ions as Synthetic Intermediates.I.α- [(alkynyl)dicobalthexacarbonyl] Carbenium Ions as Propargylating Agents, Tetrahedron Letters, 18(48), 4163- 4165, 1977.
• Aoyogi, Y., Mizusaki, T., Ohta, A., Facile and Efficient Synthesis of Pyrroles and Indoles via Palladium- Catalyzed Oxidation of Hydroxy-Enamines and –Amines, Tetrahedron Letters, 37(51), 9203-9206, 1996.
• Andrew, R.J., Synthesis of Trifluoromethylpyrroles and Related Heterocycles from 4-Ethyloxy-1,1,1- trifluorobut-3-ene-2-one, Tetrahedron, 56(37), 7267-7272, 2000.
• Hojo, M., Masuda, R., Okada, E., Sakaguchi, S., Narumiya, H., Morimoto, K., O-N, S-N and N-N exchange reactions at olefinic carbon atoms: Facile synthetic method for β-trifluoroacetylvinylamines, Tetrahedron Letters, 30(45), 6173-6176, 1989.
• Farcas, S., Namy, J.L., Samarium Diiodide Promoted Reactions of a Diphenyl α-Iminoketone, A New Synthesis of Some Pyrrole Derivaties, Tetrahedron, 57(23), 4881-4888, 2001.
• Deryagina, E.N., Russavakaya, N.V., Vvedenskii, V.Y., Synthesis of 1-[5-(2,2′-Dithienl]-1-Ethanone Oxime and Its Reaction with Acetylene, Russian Journal of Organic Chemistry, 35(8), 1225-1227, 1999.
• Gabriele, B., Salerno, G., Fazio, A., Bossio, M.R., Palladium-Catalyzed Cycloisomerization of (Z)-(2-en-4- ynyl)amines: A New Synthesis of Substituted Pyrroles, Tetrahedron Letters, 42(7), 1339-1341, 2001.
• Danks, T.N., Microwave Assisted Synthesis of Pyrroles, Tetrahedron Letters, 40(20), 3957-3960, 1999.
• Chen, B.C., Guang-Zhi, Z., Katritzky, A.R., Yousaf, T.I., An H-1, C-13 and N-15 NMR Study of the Paal- Knorr Condensation of Acetonylacetone with Primary Amines, Tetrahedron, 42(2), 623-628, 1986.
• Ranu, B.C., Hajra, A., Synthesis of Alkyl-Substitued Pyrroles by Three-Component Coupling of Carbonyl Compound, Amine and Nitro-Alkane/Alkene On a Solid Surface of Silica Gel/Alumina Under Microwave Irradiation, Tetrahedron, 57(22), 4767-4773, 2001.
• Xu, X., Zhang, Y., Synthesis of 3H-Pyrroles Promoted by Samarium/Cat. Iodine System, Synthetic Commun., 32(17), 2643-2650, 2002.
• Azizian, J., Karimi, A.R., Arefrad, H., Mohammadi, A.A., Mohammadizadeh, M.R., A Novel One-Pot, Four Component Synthesis of Some Densely Functionalized Pyrroles, Molecular Diversity, 6, 223-226, 2003.
• Matiychuk, V.S., Martyak, R.L., Obushak, N.D., Ostapiuk, Y.V., Pidlypnyi, N.I., 3-Aryl-2-Chloropropanals in Hantzsch Synthesis of Pyrroles, Chemistry of Heterocyclic Compound, 40(9), 1218-1219, 2004.
• Song, G., Wang, B., Fe3+-Montmorillonite as Effective, Recyclable Catalyst for Paal-Knorr Pyrrole Synthesis Under Mild Conditions, Synthetic Commun., 35, 1051-1057, 2005.