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Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones

Publication ,  Journal Article
Friary, R; McPhail, AT; Seidl, V
Published in: Collection of Czechoslovak Chemical Communications
1993

2-methylthio-2-imidazoline and 2-methylthio-1,4,5,6-tetrahydro-2-pyrimidine amidated 2-chloro-3-pyridine- and 2-chloro-3-pyrazinecarbonyl chlorides. The products reacted with aromatic amines forming a series of tricyclic, linearly fused -aryl pyrimidones. Included among these pyrimidones were 10-aryl-2,3-dihydroimidazo[1,2-]pyrido[2,3-]pyrimidin-5(10)-ones, 11-aryl-2,3,4,11-tetrahydropyrido-[2,3-]pyrimido[1,2-]pyrimidin-6(6)-ones, 10-aryl-2,3-dihydroimidazo[1,2-]pyrazino[2,3-]pyrimidin-5(10)-ones and 11-aryl-2,3,4,11-tetrahydropyrimido-[1,2-]pyrazino[2,3-]pyrimidin-6(6)-ones. 4,5,6,7-Tetrahydro-2-(mythylthio)-1-1,3-diazepine amidated the ethyl hydrogen carbonate of 2-(phenylamino)-3-pyridinecarboxylic acid, forming 12-phenyl-2,3,4,5-tetrahydropyrido[2',3':4,5]pyrimido[1,2-][1,3]diazepine-7(12)-one. A single crystal X-ray analysis and an unambiguous synthesis established the structure of the linearly fused isomer 10-phenyl-2,3-dihydroimidazo[1,2-]pyrido[2,3-]pyrimidin-5(10)-one.

Duke Scholars

Published In

Collection of Czechoslovak Chemical Communications

DOI

EISSN

1212-6950

ISSN

0010-0765

Publication Date

1993

Volume

58

Issue

5

Start / End Page

1133 / 1150

Publisher

Institute of Organic Chemistry & Biochemistry

Related Subject Headings

  • General Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

APA
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ICMJE
MLA
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Friary, R., McPhail, A. T., & Seidl, V. (1993). Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones. Collection of Czechoslovak Chemical Communications, 58(5), 1133–1150. https://doi.org/10.1135/cccc19931133
Friary, Richard, Andrew T. McPhail, and Vera Seidl. “Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones.” Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1133–50. https://doi.org/10.1135/cccc19931133.
Friary R, McPhail AT, Seidl V. Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones. Collection of Czechoslovak Chemical Communications. 1993;58(5):1133–50.
Friary, Richard, et al. “Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones.” Collection of Czechoslovak Chemical Communications, vol. 58, no. 5, Institute of Organic Chemistry & Biochemistry, 1993, pp. 1133–50. Crossref, doi:10.1135/cccc19931133.
Friary R, McPhail AT, Seidl V. Novel Syntheses of Tricyclic, N-Aryl, Pyridine- and Pyrazine-Fused Pyrimidones. Collection of Czechoslovak Chemical Communications. Institute of Organic Chemistry & Biochemistry; 1993;58(5):1133–1150.

Published In

Collection of Czechoslovak Chemical Communications

DOI

EISSN

1212-6950

ISSN

0010-0765

Publication Date

1993

Volume

58

Issue

5

Start / End Page

1133 / 1150

Publisher

Institute of Organic Chemistry & Biochemistry

Related Subject Headings

  • General Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences