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Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene

Hantzsch condensation of two equivalents of methyl-3-aminocrotonate with (m- and p)-methoxybenzaldehyde afforded the expected products 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(m-methoxyphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-methoxyphenyl)-1,4-dihydropyridine, whereas o-...

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Autores principales: Filipan-Litvić, Mirela, Litvić, Mladen, Cepanec, Ivica, Vinković, Vladimir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2007
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149142/
https://www.ncbi.nlm.nih.gov/pubmed/18065957
http://dx.doi.org/10.3390/12112546
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author Filipan-Litvić, Mirela
Litvić, Mladen
Cepanec, Ivica
Vinković, Vladimir
author_facet Filipan-Litvić, Mirela
Litvić, Mladen
Cepanec, Ivica
Vinković, Vladimir
author_sort Filipan-Litvić, Mirela
collection PubMed
description Hantzsch condensation of two equivalents of methyl-3-aminocrotonate with (m- and p)-methoxybenzaldehyde afforded the expected products 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(m-methoxyphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-methoxyphenyl)-1,4-dihydropyridine, whereas o-methoxy-benzaldehyde produced mainly 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxy-phenyl)-4-oxa-cyclohexan-1-ene. The structure of the product, not previously reported in the literature, was determined by 1D and 2D NMR spectra and its MS fragmentation. This is the first example of cyclisation leading to a substituted pyran rather than 1,4-DHP under typical Hantzsch reaction conditions. A plausible mechanism for its formation is postulated.
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spelling pubmed-61491422018-11-19 Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene Filipan-Litvić, Mirela Litvić, Mladen Cepanec, Ivica Vinković, Vladimir Molecules Article Hantzsch condensation of two equivalents of methyl-3-aminocrotonate with (m- and p)-methoxybenzaldehyde afforded the expected products 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(m-methoxyphenyl)-1,4-dihydropyridine and 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-methoxyphenyl)-1,4-dihydropyridine, whereas o-methoxy-benzaldehyde produced mainly 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxy-phenyl)-4-oxa-cyclohexan-1-ene. The structure of the product, not previously reported in the literature, was determined by 1D and 2D NMR spectra and its MS fragmentation. This is the first example of cyclisation leading to a substituted pyran rather than 1,4-DHP under typical Hantzsch reaction conditions. A plausible mechanism for its formation is postulated. MDPI 2007-11-26 /pmc/articles/PMC6149142/ /pubmed/18065957 http://dx.doi.org/10.3390/12112546 Text en © 2007 by MDPI (http://www.mdpi.org). Reproduction is permitted for noncommercial purposes.
spellingShingle Article
Filipan-Litvić, Mirela
Litvić, Mladen
Cepanec, Ivica
Vinković, Vladimir
Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title_full Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title_fullStr Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title_full_unstemmed Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title_short Hantzsch Synthesis of 2,6-Dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a Novel Cyclisation Leading to an Unusual Formation of 1-Amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
title_sort hantzsch synthesis of 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o-methoxyphenyl)-1,4-dihydropyridine; a novel cyclisation leading to an unusual formation of 1-amino-2-methoxy-carbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149142/
https://www.ncbi.nlm.nih.gov/pubmed/18065957
http://dx.doi.org/10.3390/12112546
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