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Molecules 2007, 12(11), 2546-2558; https://doi.org/10.3390/12112546

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-methoxycarbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene

1
BELUPO Pharmaceuticals, Inc. R&D, Danica 5, 48000 Koprivnica, Croatia
2
Institute Ruđer Bošković, Bijenička c. 54, 10002 Zagreb, Croatia
*
Author to whom correspondence should be addressed.
Received: 9 November 2007 / Revised: 22 November 2007 / Accepted: 23 November 2007 / Published: 26 November 2007
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Abstract

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 theliterature, was determined by 1D and 2D NMR spectra and its MS fragmentation. This isthe first example of cyclisation leading to a substituted pyran rather than 1,4-DHP undertypical Hantzsch reaction conditions. A plausible mechanism for its formation ispostulated. View Full-Text
Keywords: Hantzsch condensation; intramolecular Michael addition; deprotonation; substituted pyrane. Hantzsch condensation; intramolecular Michael addition; deprotonation; substituted pyrane.
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Filipan-Litvić, M.; Litvić, M.; Cepanec, I.; Vinković, V. 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-methoxycarbonyl-3,5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene. Molecules 2007, 12, 2546-2558.

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