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Journal

2005 | 3 | 2 | 311-325

Article title

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

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EN

Abstracts

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.

Publisher

Journal

Year

Volume

3

Issue

2

Pages

311-325

Physical description

Dates

published
1 - 6 - 2005
online
1 - 6 - 2005

Contributors

author
  • 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
author
  • 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

References

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Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_BF02475999
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