Synthesis of some new pyridines, thienopyridines and pyridothienopyrimidines bearing 1,3-diphenyl-1H-pyrazole moiety

AshEse Journal of Physical Science                                                                   
Vol. 2(1), pp. 033-041, January, 2016    
ISSN 2059-7827                                                                                                        
© 2016 AshEse Visionary Limited  
 
Full Length Research

Elham A. Al-Taifi,1Eman A. Thabet,2Etify A. Bakhite3* and Talaat I. El-Emary3

1Department of Chemistry, Faculty of Science, Sana’a University, Sana’a,  Yemen

2Department of Chemistry, Faculty of Science, Taiz University, Taiz,  Yemen

3Department of Chemistry, Faculty of Science, Assiut University, Assiut71516,  Egypt

*Corresponding author. E-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.

Received November, 2015; Accepted December, 2015

 

Abstract: 1-phenyl/(2-thienyl)-3-(1,3-Diphenyl-1H-pyrazol-4-yl)-2-propen-1-ones (3a,b) were prepared. Reaction of 3b with hydroxyl amine, phenyl hydrazine or ethyl cyanoacetate gave the corresponding heterocyclic compounds 4, 5 and 6 respectively. Treatment compounds 3a,b with cyanothioacetaimde furnished 3-cyano-4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-phenyl/(2-thienyl)pyridine-2(1H)-thiones (7a,b). Reaction of 7a,b with chloroacetamide, p-methylphenacyl chloride, ethyl chloroacetate, chloro-N-(aryl)acetamides gave S-substituted methylthiopyridines 8a-g. Upon treatment of compounds 8a-g with sodium ethoxide in boiling ethanol, they underwent intramolecular Thorpe-Zeigler cyclization giving 2-functionalized 3-amino-4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-phenyl/(2-thienyl)thieno[2,3-b]pyridines (9a-g). Compounds 9a,c were subjected to some sequence reactions to produce new  pyrazolylpyridothienopyrimidines 10a-c, 11a,b and 13-16.

Key words: 1,3-diphenylpyrazole, 3-cyanopyridine-2(1H)-thiones, pyrazolylthienopyridines, pyrazolylpyridothienopyrimidines

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