Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate

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Title:Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate
Creators:
Heleyová, Katarína
Ilavský, Dušan
Bobošík, Vladimír
Prónayová, Naďa
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 3, pp. 371-380
Uncontrolled Keywords:Oxazoloquinolones, Gould-Jacobs reaction

Abstract

Nucleophilic reaction of 5-amino- and 6-amino-2-substituted benzoxazoles <strong>1</strong> and <strong>2</strong> with 3-ethoxymethylene-2,4-pentanedione (<strong>3</strong>) gave compounds <strong>5</strong> and <strong>6</strong>. Compounds <strong>1</strong> and <strong>2</strong> reacted with ethyl ethoxymethylene-3-oxobutanoate (<strong>4</strong>) under formation of compounds <strong>7</strong>and <strong>8</strong>. The substitution products <strong>7</strong> and <strong>8</strong> underwent thermal cyclization at high temperature (boiling mixture of diphenyl ether and biphenyl) to give angularly and linearly annelated derivatives of 5-acetyl-4-oxo-oxazolo[4,5-<i>f</i>]quinoline <strong>9</strong> and 7-acetyl-8-oxo-oxazolo[5,4-<i>g</i>]quinoline <strong>10</strong> (from <strong>7</strong>), and derivatives of 8-acetyl-9-oxo-oxazolo[5,4-<i>f</i>]quinoline <strong>11</strong> and 6-acetyl-5-oxo-oxazolo[4,5-<i>g</i>]quinoline <strong>12</strong> (from <strong>8</strong>). The structure of the substitution products is discussed on the basis of their spectral characteristics (<sup>1</sup>H and <sup>13</sup>C NMR, IR, UV, MS).

Title:Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate
Creators:
Heleyová, Katarína
Ilavský, Dušan
Bobošík, Vladimír
Prónayová, Naďa
Uncontrolled Keywords:Oxazoloquinolones, Gould-Jacobs reaction
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:61
Number:3
Page Range:pp. 371-380
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960371UNSPECIFIED
ID Code:939
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Heleyová, Katarína; Ilavský, Dušan; Bobošík, Vladimír; Prónayová, Naďa (1996) Gould-Jacobs Reaction of 5- and 6-Amino-2-substituted Benzoxazoles. II. Reaction with 3-Ethoxymethylene-2,4-pentanedione and Ethyl 2-Ethoxymethylene-3-oxobutanoate. Collection of Czechoslovak Chemical Communications, 61 (3). pp. 371-380. ISSN 0010-0765

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