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2005 | 3 | 2 | 311-325
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
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.
Wydawca

Czasopismo
Rocznik
Tom
3
Numer
2
Strony
311-325
Opis fizyczny
Daty
wydano
2005-06-01
online
2005-06-01
Twórcy
  • Department of Chemistry of Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK 91701, Trnava, Slovak Republic
  • Department of Chemistry of Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK 91701, Trnava, Slovak Republic
autor
  • Department of Organic Chemistry of Faculty of Chemical Technology, University of Pardubice, CZ 52210, Pardubice, Czech Republic
  • Department of Chemistry of Faculty of Natural Sciences, University of St. Cyril and Methodius in Trnava, SK 91701, Trnava, Slovak Republic, krutosik@ucm.sk
Bibliografia
  • [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.
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  • [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/cccc19991135[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.
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  • [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)60007-0[Crossref]
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  • [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/cccc19971612[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]
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  • [28] P. Gajdoš, J. Miklovič and A. Krutošíková: “Reactions of 5-[3-(Trifluoromethyl)phenyl]furan-2-carbaldehyde”, Khim. Geterotsikl. Soed., submitted for paper.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02475999
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