Preparation of New Optically Active Furanoids Containing Various Aza-Heterocyclic Moieties

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Title:Preparation of New Optically Active Furanoids Containing Various Aza-Heterocyclic Moieties
Creators:
Werfeli, Ali
Čejka, Jan
Klecán, Ondřej
Kratochvíl, Bohumil
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 6, pp. 894-912
Uncontrolled Keywords:Absolute configuration, Furans, X-Ray diffraction, Isoxazoles, Pyridin-2(1<i>H</i>)-ones, Ferricyanide oxidation, 1,4-Dihydropyridines, Gabriel synthesis, Schiff bases

Abstract

The aldehyde <strong>2</strong> prepared from [5-(2,3-<i>O</i>-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran-3-yl]methanol (<strong>1</strong>) was converted to <i>E</i>,<i>Z</i>-oximes <strong>3</strong>, <strong>4</strong> and imine derivative <strong>5</strong> by the reaction with hydroxylamine and pyridin-2-yl amine, respectively. The Knoevenagel reaction with malonic acid afforded exclusively the 3-substituted acrylic acid <strong>6</strong> while corresponding Hantzsch 1,4-dihydropyridines <strong>7</strong> and <strong>8</strong> were obtained by the reaction of aldehyde <strong>2</strong> with ethyl acetoacetate or acetylacetone and ammonia. 3,5-Dicyano-1,4-dihydropyridine derivative <strong>9</strong> was isolated only in forms of hydrates after the reaction of aldehyde <strong>2</strong> with 3-aminocrotonitrile. 1,4-Dihydropyridines <strong>7</strong> and <strong>9</strong> were aromatized to corresponding pyridines <strong>10</strong> and <strong>11</strong>. Isoxazoles <strong>12</strong>, <strong>13</strong> and isoxazolines <strong>14</strong>, <strong>15</strong> were prepared by 1,3-cycloaddition of appropriate dienophiles to a nitrile oxide generated from aldoximes <strong>3</strong>,<strong> 4</strong>. Ferricyanide oxidation of 1-{[5-(2,3-<i>O</i>-isopropylidene-β-D-erythrofuranosyl)-2-methylfuran-3-yl]methyl}pyridinium chloride (<strong>17a</strong>), -3-methylpyridinium chloride (<strong>19a</strong>) and the corresponding isoquinolinium chloride <strong>21a</strong> gave optically active pyridin-2(1<i>H</i>)-ones <strong>22</strong>, <strong>23</strong> and 2<i>H</i>-isoquinolone derivative <strong>24</strong> while the procedure with 2-methylpyridinium salt <strong>18a</strong> and 4-methylpyridinium salt <strong>20a</strong> led to complex mixtures of products. Reaction of 2,4,6-triphenylpyrylium perchlorate with furanoid amine <strong>26</strong> afforded a mixture of major 2,4,6-triphenylpyridine, minor pyridinium perchlorate <strong>25</strong> and primary alcohol <strong>1</strong>. The absolute configuration of the studied compounds has been confirmed by X-ray analysis of the Schiff base <strong>5</strong>.

Title:Preparation of New Optically Active Furanoids Containing Various Aza-Heterocyclic Moieties
Creators:
Werfeli, Ali
Čejka, Jan
Klecán, Ondřej
Kratochvíl, Bohumil
Kuthan, Josef
Uncontrolled Keywords:Absolute configuration, Furans, X-Ray diffraction, Isoxazoles, Pyridin-2(1<i>H</i>)-ones, Ferricyanide oxidation, 1,4-Dihydropyridines, Gabriel synthesis, Schiff bases
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:6
Page Range:pp. 894-912
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970894UNSPECIFIED
ID Code:1172
Item Type:Article
Deposited On:06 Feb 2009 17:07
Last Modified:06 Feb 2009 16:07

Citation

Werfeli, Ali; Čejka, Jan; Klecán, Ondřej; Kratochvíl, Bohumil; Kuthan, Josef (1997) Preparation of New Optically Active Furanoids Containing Various Aza-Heterocyclic Moieties. Collection of Czechoslovak Chemical Communications, 62 (6). pp. 894-912. ISSN 0010-0765

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