Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds

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Title:Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds
Creators:
Svoboda, Jiří
Nič, Miloslav
Paleček, Jaroslav
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 3, pp. 592-599

Abstract

The Dieckmann condensation of methyl [(2-methoxycarbonyl)phenyl]-X-acetates <i>Ia-Ih</i> (X = O, S, SO<sub>2</sub>, NH, NCH<sub>3</sub>) initiated by action of magnesium methoxide, ethoxide, isopropoxide and other basic reagents have been studied under various conditions. Whereas magnesium methoxide has comparable efficiency as sodium methoxide and potassium tert-butoxide in syntheses of benzoheterocyclic compounds <i>IIa-IIh</i>, magnesium ethoxide gives the ethyl ester <i>IIb</i> in medium yield, and magnesium isopropoxide is quite inefficient in the condensation reaction. The alkylation of the esters <i>IIa, IId,</i> and <i>IIg</i> with methyl chloroacetate in the presence of sodium hydride in dimethylformamide gives the diesters <i>IIi - IIk</i> which on action by potassium tert-butoxide undergo the cyclization reaction to give esters <i>III</i>.

Title:Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds
Creators:
Svoboda, Jiří
Nič, Miloslav
Paleček, Jaroslav
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:58
Number:3
Page Range:pp. 592-599
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19930592UNSPECIFIED
ID Code:183
Item Type:Article
Deposited On:06 Feb 2009 16:58
Last Modified:06 Feb 2009 15:58

Citation

Svoboda, Jiří; Nič, Miloslav; Paleček, Jaroslav (1993) Application of Magnesium Alkoxides to Syntheses of Benzoheterocyclic Compounds. Collection of Czechoslovak Chemical Communications, 58 (3). pp. 592-599. ISSN 0010-0765

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