Preferences help
enabled [disable] Abstract
Number of results
2005 | 3 | 2 | 311-325
Article title

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

Title variants
Languages of publication
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.
Physical description
1 - 6 - 2005
1 - 6 - 2005
  • [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.
  • [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.
  • [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. [Crossref]
  • [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.
  • [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.[Crossref]
  • [6] R. Sleziak and A. Krutošíková: “Cycloaddition Reactions of Furo[3,2-b]pyrroles”, Collect. Czech. Chem. Commun., Vol. 64, (1999), pp. 321–328.[Crossref]
  • [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.[Crossref]
  • [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.
  • [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.[Crossref]
  • [10] A. Krutošíková: “Synthesis and Reactions of Condensed Furan Derivatives”, Collect. Czech. Chem. Commun., Vol. 55, (1990), pp. 597–621.[Crossref]
  • [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.[Crossref]
  • [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. [Crossref]
  • [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.[Crossref]
  • [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.
  • [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.[Crossref]
  • [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.[Crossref]
  • [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. [Crossref]
  • [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. [Crossref]
  • [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. [Crossref]
  • [20] A. Krutošíková, J. Kováč and M. Dandárová: “Synthesis and Reactions of Furocondensed Derivatives”, Collect. Czech. Chem. Commun., Vol. 49, (1984), pp. 65–70. [Crossref]
  • [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. [Crossref]
  • [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.
  • [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.[Crossref]
  • [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.
  • [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. [Crossref]
  • [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. [Crossref]
  • [27] D. Azarifar and H. Ghasemnejad: “Microwave-Assisted Synthesis of Some 3,5-Arylated 2-Pyrazolines”, Molecules, Vol. 8, (2003), pp. 642–648. [Crossref]
  • [28] P. Gajdoš, J. Miklovič and A. Krutošíková: “Reactions of 5-[3-(Trifluoromethyl)phenyl]furan-2-carbaldehyde”, Khim. Geterotsikl. Soed., submitted for paper.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.