Publikace detail

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles:Synthesis and Reactions

Autoři: Gajdoš Peter | Pavlíková Soňa | Bureš Filip | Krutošíková Alžbeta

Rok: 2005

Druh publikace: článek v odborném periodiku

Název zdroje: Central European Journal of Chemistry

Název nakladatele: Springer

Strana od-do: 311-325

Tituly:

Jazyk	Název	Abstrakt	Klíčová slova
cze	2-[3-(Trifluoromethyl)fenyl]furo[3,2-b]pyrroly:Syntéza a reakce	The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl-4H-furo[3,2-b]pyrrole-5-carboxylate (la) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds la-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[l,2d][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.
eng	2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles:Synthesis and Reactions	The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl-4H-furo[3,2-b]pyrrole-5-carboxylate (la) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds la-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[l,2d][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.	2-[3-(trifluoromethyl)phenyl]furo[3,2-bjpyrroles; hydrazides; hydrazones; cycloaddition; condensation; phase transfer catalysis; microwave irradiation; H-1 and C-13 NMR spectra

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