Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid

4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on s...

Full description

Bibliographic Details
Main Authors: Alžbeta Krutošíková, Heinz Sterk, Zita Puterová
Format: Article
Language:English
Published: MDPI AG 2004-01-01
Series:Molecules
Subjects:
Online Access:http://www.mdpi.com/1420-3049/9/1/11/
_version_ 1828423342259961856
author Alžbeta Krutošíková
Heinz Sterk
Zita Puterová
author_facet Alžbeta Krutošíková
Heinz Sterk
Zita Puterová
author_sort Alžbeta Krutošíková
collection DOAJ
description 4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with “classical†conditions. The results show that microwave irradiation shortens the reaction times while affording comparable yields. Elementary analysis, UV, IR and 1D NMR proved the structure of new synthesised compounds. 2D NMR spectroscopic measurements confirmed that the configuration at the carbon-carbon double bond corresponds to the pure E isomers of the products.
first_indexed 2024-12-10T16:00:16Z
format Article
id doaj.art-b8e9ad18515f4dbd830586c5c72bb866
institution Directory Open Access Journal
issn 1420-3049
language English
last_indexed 2024-12-10T16:00:16Z
publishDate 2004-01-01
publisher MDPI AG
record_format Article
series Molecules
spelling doaj.art-b8e9ad18515f4dbd830586c5c72bb8662022-12-22T01:42:27ZengMDPI AGMolecules1420-30492004-01-0191112110.3390/90100011Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric AcidAlžbeta KrutošíkováHeinz SterkZita Puterová4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with “classical†conditions. The results show that microwave irradiation shortens the reaction times while affording comparable yields. Elementary analysis, UV, IR and 1D NMR proved the structure of new synthesised compounds. 2D NMR spectroscopic measurements confirmed that the configuration at the carbon-carbon double bond corresponds to the pure E isomers of the products.http://www.mdpi.com/1420-3049/9/1/11/5-Arylfuran-2-carboxaldehydesfuro[32-b]pyrrole-2-carboxaldehydesfuro- [23-b]pyrrole-2-carboxaldehydeshippuric acidmicrowave irradiation13-oxazol- 5(4H)-onesfuro[32-b]pyrrole-5-carboxylatesfuro[23-b]pyrrole-5-carboxylates1H- and 13 C-NMRCOSYNOESYHSQCHMBC.
spellingShingle Alžbeta Krutošíková
Heinz Sterk
Zita Puterová
Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
Molecules
5-Arylfuran-2-carboxaldehydes
furo[3
2-b]pyrrole-2-carboxaldehydes
furo- [2
3-b]pyrrole-2-carboxaldehydes
hippuric acid
microwave irradiation
1
3-oxazol- 5(4H)-ones
furo[3
2-b]pyrrole-5-carboxylates
furo[2
3-b]pyrrole-5-carboxylates
1H- and 13 C-NMR
COSY
NOESY
HSQC
HMBC.
title Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
title_full Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
title_fullStr Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
title_full_unstemmed Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
title_short Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
title_sort reaction of substituted furan 2 carboxaldehydes and furo b pyrrole type aldehydes with hippuric acid
topic 5-Arylfuran-2-carboxaldehydes
furo[3
2-b]pyrrole-2-carboxaldehydes
furo- [2
3-b]pyrrole-2-carboxaldehydes
hippuric acid
microwave irradiation
1
3-oxazol- 5(4H)-ones
furo[3
2-b]pyrrole-5-carboxylates
furo[2
3-b]pyrrole-5-carboxylates
1H- and 13 C-NMR
COSY
NOESY
HSQC
HMBC.
url http://www.mdpi.com/1420-3049/9/1/11/
work_keys_str_mv AT alaa3⁄4betakrutoaaaƒakovaƒa reactionofsubstitutedfuran2carboxaldehydesandfurobpyrroletypealdehydeswithhippuricacid
AT heinzsterk reactionofsubstitutedfuran2carboxaldehydesandfurobpyrroletypealdehydeswithhippuricacid
AT zitaputerovaƒa reactionofsubstitutedfuran2carboxaldehydesandfurobpyrroletypealdehydeswithhippuricacid