A New Approach to Imidazo[1,5-a]indole Derivatives

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Title:A New Approach to Imidazo[1,5-a]indole Derivatives
Creators:
Kutschy, Peter
Suchý, Mojmír
Dzurilla, Milan
Takasugi, Mitsuo
Kováčik, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 7, pp. 1163-1172
Uncontrolled Keywords:Isothiocyanates, Antifungal activity, Phytoalexins, Indoles, Imidazoles, Cyclization

Abstract

Reaction of indole-2-carbonyl isothiocyanate (<strong>1</strong>) with sodium methanethiolate afforded 1-thioxo-1<i>H</i>-imidazo[1,5-<i>a</i>]indol-3(2<i>H</i>)-one (<strong>3</strong>). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding <i>S</i>- and <i>N</i>-methyl derivatives <strong>4</strong> and <strong>5</strong>. <i>N</i>-(Indole-2-carbonyl)thiocarbamates and <i>N</i>-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate <strong>1</strong> with corresponding nucleophilic reagents were <i>S</i>-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained <i>N</i>-(indole- 2-carbonyl) substituted thiocarbonimidates <strong>15</strong>, <strong>16</strong> and isothioureas <strong>17</strong>-<strong>20</strong> afforded by treatment with lithium hydride in dimethylformamide the derivatives of imidazo[1,5-<i>a</i>]- indol-3-one <strong>23</strong>-<strong>28</strong> in 49-87% yields. Antifungal activity of the prepared compounds has been examined, using the fungus <i>Bipolaris leersiae</i>. 1-Methylsulfanyl-3<i>H</i>-imidazo-[1,5-<i>a</i>]- indol-3-one (<strong>4</strong>) exhibited the highest antifungal activity. <p>

Title:A New Approach to Imidazo[1,5-a]indole Derivatives
Creators:
Kutschy, Peter
Suchý, Mojmír
Dzurilla, Milan
Takasugi, Mitsuo
Kováčik, Vladimír
Uncontrolled Keywords:Isothiocyanates, Antifungal activity, Phytoalexins, Indoles, Imidazoles, Cyclization
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:65
Number:7
Page Range:pp. 1163-1172
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001163UNSPECIFIED
ID Code:1708
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:12

Citation

Kutschy, Peter; Suchý, Mojmír; Dzurilla, Milan; Takasugi, Mitsuo; Kováčik, Vladimír (2000) A New Approach to Imidazo[1,5-a]indole Derivatives. Collection of Czechoslovak Chemical Communications, 65 (7). pp. 1163-1172. ISSN 0010-0765

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