Reactions of a New Family of Amide Derivatives of Phenanthridinium Azomethine Ylides with Dipolarophiles

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Title:Reactions of a New Family of Amide Derivatives of Phenanthridinium Azomethine Ylides with Dipolarophiles
Creators:
Trávníček, Martin
Pospíšil, Jiří
Potáček, Milan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 12, pp. 1993-2006
Uncontrolled Keywords:Dimethyl fumarate, Stereochemistry, Dimethyl maleate, 1,3-Dipolar cycloadditions, Azomethine ylides, Fumaronitrile, 5-Substituted 6-phenanthridones, Phenanthridinium salts, NMR spectroscopy

Abstract

Reaction of a series of <i>N</i>-alkyl- and <i>N,N</i>-dialkylbromoacetamides <strong>1a</strong>-<strong>1e</strong> with phenanthridine afforded quaternary phenanthridinium salts <strong>2a</strong>-<strong>2e</strong>. These compounds treated with triethylamine form azomethine ylides which undergo a cycloaddition reaction with activated C=C bond, giving 3-(<i>N</i>-alkylcarbamoyl)-1,2,3,12b-tetrahydropyrrolo[1,2-<i>f</i>]phenanthridines <strong>3a</strong>-<strong>3e</strong>, <strong>4c</strong>, <strong>5c</strong>, <strong>6c</strong> or 3-(<i>N</i>-alkylcarbamoyl)-2,3-dihydropyrrolo[1,2-<i>f</i>]phenanthridine <strong>7c</strong>. Their stereochemistry was studied by NMR spectroscopy. The best results were obtained with fumaronitrile as a dipolarophile. It has been found that the ylides react in <i>syn</i> conformations but if 1-adamantyl moiety is bound to the ylide, it reacts in <i>anti</i> conformation, too. The azomethine ylides show a very poor reactivity towards dimethyl fumarate or dimethyl maleate. Yet we could prepare products for ylide bearing 1-adamantyl group. <p>

Title:Reactions of a New Family of Amide Derivatives of Phenanthridinium Azomethine Ylides with Dipolarophiles
Creators:
Trávníček, Martin
Pospíšil, Jiří
Potáček, Milan
Uncontrolled Keywords:Dimethyl fumarate, Stereochemistry, Dimethyl maleate, 1,3-Dipolar cycloadditions, Azomethine ylides, Fumaronitrile, 5-Substituted 6-phenanthridones, Phenanthridinium salts, NMR spectroscopy
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:64
Number:12
Page Range:pp. 1993-2006
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991993UNSPECIFIED
ID Code:1611
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Trávníček, Martin; Pospíšil, Jiří; Potáček, Milan (1999) Reactions of a New Family of Amide Derivatives of Phenanthridinium Azomethine Ylides with Dipolarophiles. Collection of Czechoslovak Chemical Communications, 64 (12). pp. 1993-2006. ISSN 0010-0765

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