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

Filipan-Litvić, Mirela; Litvić, Mladen; Cepanec, Ivica; Vinković, Vladimir

doi:10.3390/12112546

Pregled bibliografske jedinice broj: 311768

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

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-methoxycarbonyl- 3, 5-bis(o-methoxyphenyl)-4-oxa-cyclohexan-1-ene // Molecules, 12 (2007), 11; 2546-2558 doi:10.3390/12112546 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 311768 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
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

Autori
Filipan-Litvić, Mirela ; Litvić, Mladen ; Cepanec, Ivica ; Vinković, Vladimir

Izvornik
Molecules (1420-3049) 12 (2007), 11; 2546-2558

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Hantzsch condensation ; intramolecular Michael addition ; deprotonation ; substituted pyrane

Sažetak
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-methoxybenzaldehyde 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
098-0982904-2910 - Kiralni organski materijali – sintetska, strukturna i funkcionalna istraživanja (Vinković, Vladimir, MZOS ) ( CroRIS)

Ustanove:
Institut "Ruđer Bošković", Zagreb

Profili:

Vladimir Vinković (autor)