Next Article in Journal
The Drug Release Profile from Calcium-induced Alginate Gel Beads Coated with an Alginate Hydrolysate
Previous Article in Journal
Synthesis of New L-Ascorbic Ferulic Acid Hybrids
Molecules 2007, 12(11), 2546-2558; doi:10.3390/12112546
Article

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
,
1,* , 1
 and
2
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
View Full-Text   |   Download PDF [104 KB, uploaded 18 June 2014]   |  

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.
Keywords: Hantzsch condensation; intramolecular Michael addition; deprotonation; substituted pyrane. Hantzsch condensation; intramolecular Michael addition; deprotonation; substituted pyrane.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert