Abstract
The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.
[1] A. Krutošíková: “Bicyclic 5-5 Systems: Two Heteroatoms 1:1”, In: C.A. Ramsden (Ed.): Comprehensive Heterocyclic Chemistry II, Vol. 7, Pergamon, Oxford, 1996, p. 1–47. Search in Google Scholar
[2] A. Krutošíková, M. Dandárová and J. Alföldi: “Substituted Vinyl Azides in the Synthesis of Condensed Nitrogen Heterocycles”, Chem. Papers, Vol. 48, (1994), pp. 268–273. Search in Google Scholar
[3] A. Krutošíková and M. Dandárová: “Substituted Vinyl Azides in the Synthesis of Furo[3,2-b:4,5-b′]dipyrroles and Pyrrolo[2′,3′:4,5]furo[3,2-c]pyridines”, Heterocycles, Vol. 48, (1994), pp. 1695–1700. Search in Google Scholar
[4] A. Krutošíková and M. Dandárová: “Reactions of Methyl 2-Formylfuro[3,2-b]pyrrole-5-carboxylates”, Chem Papers, Vol. 50, (1996), pp. 72–76. Search in Google Scholar
[5] A. Krutošíková, C.A. Ramsden, M. Dandárová and A. Lyčka: “Synthesis and Reactions of Furo[2,3-b]pyrroles”, Molecules, Vol. 2, (1997), pp. 69–79. http://dx.doi.org/10.3390/2040006910.3390/20400069Search in Google Scholar
[6] R. Sleziak and A. Krutošíková: “Cycloaddition Reactions of Furo[3,2-b]pyrroles”, Collect. Czech. Chem. Commun., Vol. 64, (1999), pp. 321–328. http://dx.doi.org/10.1135/cccc1999032110.1135/cccc19990321Search in Google Scholar
[7] R. Sleziak, S. Balá ziová and A. Krutošíková: “Reactions of Furo[3,2-b]pyrrole and Furo[2,3-b]pyrrole-type Aldehydes”, Collect. Czech. Chem. Commun., Vol. 64, (1999), pp. 1135–1146. http://dx.doi.org/10.1135/cccc1999113510.1135/cccc19991135Search in Google Scholar
[8] R. Sleziak, A. Krutošíková, M.K. Cyranski and T.M. Krygovski: “Furo[3,2-b]pyrrole Derivatives. Syntheses and Reactions in the Furan and Pyrrole Ring”, Polish. J. Chem., Vol. 74, (2000), pp. 207–217. Search in Google Scholar
[9] A. Krutošíková, M. Dandárová, J. Alföldi and J. Kováč: “Addition and Cycloaddition of Furo[3,2-b]pyrroles and Their Benzo[b]analogues: An NMR Study of Structure of Products”, Collect. Czech. Chem. Commun., Vol. 53, (1988), pp. 1770–1778. http://dx.doi.org/10.1135/cccc1988177010.1135/cccc19881770Search in Google Scholar
[10] A. Krutošíková: “Synthesis and Reactions of Condensed Furan Derivatives”, Collect. Czech. Chem. Commun., Vol. 55, (1990), pp. 597–621. http://dx.doi.org/10.1135/cccc1990059710.1135/cccc19900597Search in Google Scholar
[11] S. Soth, M. Farnier and C. Paulmier: “Recherches en série hétérocyclique. XXIX. Sur des voies d'accés à des thiéno. Sélénolo, furo et pyrrolepyrroles”, Can. J. Chem., Vol. 56, (1978), pp. 1429–1434. http://dx.doi.org/10.1139/v78-23410.1139/v78-234Search in Google Scholar
[12] H. Behringer and E. Meinestsberger: “Űber die Reaktionen von Cyclopropen(thi)onen mit 1,2-Dithiol-Verbindungen: Thieno[3,2-b]thiophene, Thieno[3,2-b]furane, 4H-Furo[3,2-b]pyrrole und 1,2-Dithiol-3-(thi)one sowie andere Schwefelheterocyclen”, Liebigs Ann. Chem., Vol. 2, (1982), pp. 315–341. Search in Google Scholar
[13] M. Welch and R.S. Phillips: “Enzymatic Syntheses of 6-(4H-Selenolo[3,2-b]pyrrolyl)-L-alanine, 6-(4H-Selenolo[2,3-b]pyrrolyl)-L-alanine, and 6-(4H-Furo[3,2-b]pyrrolyl)-L-alanine”, Bioorg. Med. Chem. Lett., Vol. 9, (1999), pp. 637–640. http://dx.doi.org/10.1016/S0960-894X(99)00067-010.1016/S0960-894X(99)00067-0Search in Google Scholar
[14] M. Welch and R.S. Phillips: “Improved syntheses of [3,2-b]- and [2,3-b]-fused selenolo-and thienopyrroles and of furo[3,2-b]pyrrole”, Heterocycl. Commun., Vol. 5, (1999), pp. 305–310. Search in Google Scholar
[15] K.L. Milkiewicz, D.J. Parks and T.B. Lu: “Synthesis of a novel series of tetrasubstituted furo[2,3-b]pyrroles”, Tetrahedron Lett., Vol. 44, (2003), pp. 4257–4260. http://dx.doi.org/10.1016/S0040-4039(03)00895-510.1016/S0040-4039(03)00895-5Search in Google Scholar
[16] E.S.H. El Ashry, N. Rashed, M. Taha and E. Ramadan: “Condensed 1,2,4-Triazines: I. Fused to Heterocycles with Three-, Four-, and Five-Membered Rings”, Adv. Heterocycl. Chem., Vol. 59, (1994), pp. 39–177. http://dx.doi.org/10.1016/S0065-2725(08)60007-010.1016/S0065-2725(08)60007-0Search in Google Scholar
[17] E.S.H. El Ashry, N. Rashed, A. Mousaad and E. Ramadan: “Condensed 1,2,4-Triazines: II. Fused to Heterocycles with Six-, and Seven-Membered Rings and Fused to Two Heterocyclic Rings”, Adv. Heterocycl. Chem., Vol. 61, (1994), pp. 207–326. Search in Google Scholar
[18] A. Krutošíková, J. Kováč, M. Dandárová and M. Bobál'ová: “Synthesis and Reactions of Substituted Benzofuro[3,2-b]pyrrole Derivatives”, Collect. Czech. Chem. Commun., Vol. 47, (1982), pp. 3288–3296. Search in Google Scholar
[19] A. Krutošíková, J. Kováč and E. Král'ovičová: “The Synthesis and Reactions of Arylfurocondensed Derivatives”, Collect. Czech. Chem. Commun., Vol. 48, (1983), pp. 1878–1884. Search in Google Scholar
[20] A. Krutošíková, J. Kováč and M. Dandárová: “Synthesis and Reactions of Furocondensed Derivatives”, Collect. Czech. Chem. Commun., Vol. 49, (1984), pp. 65–70. Search in Google Scholar
[21] A. Koreňová, A. Krutošíková, M. Dandárová and J. Kováč: “Synthesis and Reactions of Furocondensed Systems Containing Indole Skeleton”, Collect. Czech. Chem. Commun., Vol. 49, (1984), pp. 1529–1535. Search in Google Scholar
[22] A. Krutošíková, J. Kováč and P. Banák: “Furan derivatives CXXVI. Synthesis and reactions of 3,4-dichlorophenyl-substituted furocondensed derivatives”, Chem. zvesti, Vol. 38, (1984), pp. 707–713. Search in Google Scholar
[23] A. Krutošíková, S. Mastik, M. Dandárová and A. Lyčka: “Synthesis and Reactions of 8-Hydrazinofuro[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazines”, Collect. Czech. Chem. Commun., Vol. 62, (1997), pp. 1612–1622. http://dx.doi.org/10.1135/cccc1997161210.1135/cccc19971612Search in Google Scholar
[24] D. Zbojek, R. Gašparová, M. Lácová, K. Král'ová, A. Gatial, B. Horváth and A. Krutošíková: “Reactions of substituted furo[3,2-b]pyrrole-5-carboxhydrazides and their biological activity”, Arkivoc, submitted for publication. 10.2478/BF02475192Search in Google Scholar
[25] D. Villemin, B. Martin and N. Bar: “Application of Microwave in Organic Synthesis. Dry Synthesis of 2-Arylmethylene-3(2)-napthofuranones”, Molecules, Vol. 3, (1998), pp. 88–93. Search in Google Scholar
[26] M. Lacová, R. Gašparová, S. Loos, T. Liptay and N. Prónayová: “Effect of Microwave Irradiation on the Condensation of 6-Substituted 3-Formylchromones with Some Fivemembered Heterocyclic Compounds”, Molecules, Vol. 8, (2000), pp. 167–178. Search in Google Scholar
[27] D. Azarifar and H. Ghasemnejad: “Microwave-Assisted Synthesis of Some 3,5-Arylated 2-Pyrazolines”, Molecules, Vol. 8, (2003), pp. 642–648. Search in Google Scholar
[28] P. Gajdoš, J. Miklovič and A. Krutošíková: “Reactions of 5-[3-(Trifluoromethyl)phenyl]furan-2-carbaldehyde”, Khim. Geterotsikl. Soed., submitted for paper. Search in Google Scholar
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