Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres

Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres

1,4-dihydropyridine derivatives constitute an important pharmacological group for the treatment of cardiovascular diseases. We have synthesised a series 4-(5'-nitro-2'-furyl)-1,4-dihydropyridine derivatives, which were characterised by ¹H-NMR. We have found that carboethoxy groups at the C-3 and C-5 on the 1,4-dihydropyridine ring show a much more complex signal in the ¹H NMR spectra, either when C-4 is a pseudo-prochiral or a chiral centre.

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Main Authors: Argüello DaSilva,Jacqueline, Saitz Barría,Claudio, Jullian,Carolina, Navarrete,Patricio, Núñez Vergara,Luis, Squella,Juan A.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2005
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000100018
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spelling oai:scielo:S0103-505320050001000182005-03-22Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centresArgüello DaSilva,JacquelineSaitz Barría,ClaudioJullian,CarolinaNavarrete,PatricioNúñez Vergara,LuisSquella,Juan A. NMR 1H NMR 1,4-dihydropyridines carboethoxy group enantiotopic methylene hydrogens 1,4-dihydropyridine derivatives constitute an important pharmacological group for the treatment of cardiovascular diseases. We have synthesised a series 4-(5'-nitro-2'-furyl)-1,4-dihydropyridine derivatives, which were characterised by ¹H-NMR. We have found that carboethoxy groups at the C-3 and C-5 on the 1,4-dihydropyridine ring show a much more complex signal in the ¹H NMR spectra, either when C-4 is a pseudo-prochiral or a chiral centre.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.16 n.1 20052005-02-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000100018en10.1590/S0103-50532005000100018
institution SCIELO
collection OJS
country Brasil
countrycode BR
component Revista
access En linea
databasecode rev-scielo-br
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region America del Sur
libraryname SciELO
language English
format Digital
author Argüello DaSilva,Jacqueline
Saitz Barría,Claudio
Jullian,Carolina
Navarrete,Patricio
Núñez Vergara,Luis
Squella,Juan A.
spellingShingle Argüello DaSilva,Jacqueline
Saitz Barría,Claudio
Jullian,Carolina
Navarrete,Patricio
Núñez Vergara,Luis
Squella,Juan A.
Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
author_facet Argüello DaSilva,Jacqueline
Saitz Barría,Claudio
Jullian,Carolina
Navarrete,Patricio
Núñez Vergara,Luis
Squella,Juan A.
author_sort Argüello DaSilva,Jacqueline
title Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
title_short Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
title_full Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
title_fullStr Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
title_full_unstemmed Unexpected diastereotopic behaviour in the ¹H NMR spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
title_sort unexpected diastereotopic behaviour in the ¹h nmr spectrum of 1,4-dihydropyridine derivatives triggered by chiral and prochiral centres
description 1,4-dihydropyridine derivatives constitute an important pharmacological group for the treatment of cardiovascular diseases. We have synthesised a series 4-(5'-nitro-2'-furyl)-1,4-dihydropyridine derivatives, which were characterised by ¹H-NMR. We have found that carboethoxy groups at the C-3 and C-5 on the 1,4-dihydropyridine ring show a much more complex signal in the ¹H NMR spectra, either when C-4 is a pseudo-prochiral or a chiral centre.
publisher Sociedade Brasileira de Química
publishDate 2005
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000100018
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