Gould-Jacobs Reaction of 5- and 6-Amino-2-substitutedBenzoxazoles. III. Reaction with 3-Ethoxy-2-cyanopropenonitrile and Ethyl 3-Ethoxy-2-cyanopropenoate

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Title:Gould-Jacobs Reaction of 5- and 6-Amino-2-substitutedBenzoxazoles. III. Reaction with 3-Ethoxy-2-cyanopropenonitrile and Ethyl 3-Ethoxy-2-cyanopropenoate
Creators:
Heleyová, Katarína
Ilavský, Dušan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 1, pp. 99-108
Uncontrolled Keywords:Oxazoloquinolones, Gould-Jacobs reaction

Abstract

Nucleophilic reaction of 5-amino- (<strong>1</strong>) and 6-amino-2-substituted benzoxazoles (<strong>2</strong>) with 3-ethoxy-2-cyanopropenonitrile (<strong>3</strong>) afforded the respective benzoxazolylaminomethylenemalononitriles <strong>5</strong> and <strong>6</strong>. The amino derivatives <strong>1</strong> and <strong>2</strong> reacted with ethyl 3-ethoxy-2-cyanopropenoate (<strong>4</strong>) to give the corresponding esters of benzoxazolylamino-2-cyanopropenoic acid <strong>7</strong> and <strong>8</strong>, respectively. The products <strong>7</strong> on thermal cyclization at 250-260 °C in a mixture of diphenyl ether and biphenyl afforded a mixture of angularly and linearly annelated 5-nitrile-4-oxooxazolo[4,5-<i>f</i>]quinoline <strong>9</strong> and 7-nitrile-8-oxooxazolo[5,4-<i>g</i>]quinoline <strong>10</strong>; under the same conditions compounds <strong>8</strong> were converted into 8-nitrile-9-oxooxazolo[5,4-<i>f</i>]quinolines <strong>11</strong> and 6-nitrile-5-oxooxazolo[4,5-<i>g</i>]quinolines <strong>12</strong>.

Title:Gould-Jacobs Reaction of 5- and 6-Amino-2-substitutedBenzoxazoles. III. Reaction with 3-Ethoxy-2-cyanopropenonitrile and Ethyl 3-Ethoxy-2-cyanopropenoate
Creators:
Heleyová, Katarína
Ilavský, Dušan
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:62
Number:1
Page Range:pp. 99-108
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19970099UNSPECIFIED
ID Code:1098
Item Type:Article
Deposited On:06 Feb 2009 17:06
Last Modified:06 Feb 2009 16:06

Citation

Heleyová, Katarína; Ilavský, Dušan (1997) Gould-Jacobs Reaction of 5- and 6-Amino-2-substitutedBenzoxazoles. III. Reaction with 3-Ethoxy-2-cyanopropenonitrile and Ethyl 3-Ethoxy-2-cyanopropenoate. Collection of Czechoslovak Chemical Communications, 62 (1). pp. 99-108. ISSN 0010-0765

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