STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES
EL-BARBARY, A., EL-NAGGAR, H. (2005). STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES. EKB Journal Management System, 29(2), 17-28. doi: 10.21608/djs.2005.156247
A.A. EL-BARBARY; H.H. EL-NAGGAR. "STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES". EKB Journal Management System, 29, 2, 2005, 17-28. doi: 10.21608/djs.2005.156247
EL-BARBARY, A., EL-NAGGAR, H. (2005). 'STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES', EKB Journal Management System, 29(2), pp. 17-28. doi: 10.21608/djs.2005.156247
EL-BARBARY, A., EL-NAGGAR, H. STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES. EKB Journal Management System, 2005; 29(2): 17-28. doi: 10.21608/djs.2005.156247

STUDIES ON SOME 1, 3, 4-OXA(THIA)DIAZOLE DERIVATIVES

Delta Journal of Science
Article 10, Volume 29, Issue 2, December 2005, Page 17-28  XML PDF (1.03 MB)
Document Type: Research and Reference
DOI: 10.21608/djs.2005.156247
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Authors
A.A. EL-BARBARY1; H.H. EL-NAGGAR2
1Chemistry Department, Faculty of Science, Tanta University, Tanta, Egypt
2Kafr El-zayat Company for Chemicals & Insecticides, Kafer El-Zayat, Egypt
Abstract
Fusion of 2-chloro-5- phenyl- 1,3,4-oxa(thia)diazoles (1a,b) with anthrax-nilic acid gave the cyclized compounds 3a,b which on thiation afforded 2-phenyl-1-oxa(thia)-3,3a,9-triaza-cyclopenta[b]naphthalene-4-thiones (4a,b).
Treatment of 1 with 4-chlorophenol and/or 4-chloro-aniline yielded compounds 5a,b and 5c,d, respectively. Condensation of 1a, b with 4-aminoacetophenone yielded 1-[4-(5-phenyl-[1,3,4]oxa(thia)diazol-2-ylamino)-phenyl]-ethanones (6a,b) which on fusion with benzaldehyde afforded the corresponding chalcones7. Reaction of compounds 8a,b and 9a,b, respectively. Refluxing 9 with Ac2O afforded N-acetylated compounds (10a, b). Reaction of 2-amino-5-phenyl-1,3, 4-oxa(thia)diazoles (11) with acyl bromides afforded 12a-d which on boiling with hydrogen bromide yielded 2,5-diphenylimidazo[2,1-b][1,3,4]oxadiazoles (13a,b).
Fusion of 11a,b with 2-phenyl-4H-3,1-benzoxazin-4-ones afforded 2-phenyl-3-(5-phenyl-[1,3,4]oxa(thia)diazol-2-yl)-3H-quinazolin-4-ones (14a,b). condensation of 11a,b with benzoyl chloride gave 15a,b which on treatment with sodium azide yielded 5-phenyl-1-(5-phenyl-[1,3,4]oxa(thia)diazol-2-yl)-1H-tetrazoles (16a,b). reacting 11a,b with phenylisothio-cyanate gave 17a,b which on condensation with malonic acid afforded 1-phenyl-3-(5-phenyl-[1,3,4]oxa(thia)diazol-2-yl)-2-thioxo-dihydro-pyrimidine-4, 6-diones (18a,b). Some of the compounds have been screened for their fungicidal activity.
Keywords
1; 3; 4-oxa(thia)diazoles; anthranilic acid; 4-aminoacetophenone; phenylisothio-cyanate; 2-phenyl-2H-3; 1-benzoxazin-4-ones
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