Synthesis of some novel 3,5-diaryl-1,2,4-triazole derivatives and investigation of their antimicrobial activities

ALPAY KARAOĞLU Ş., SERDAR M., GÜMRÜKÇÜOĞLU N., DEMİR N.

TURKISH JOURNAL OF CHEMISTRY, cilt.31, sa.3, ss.0-326, 2007 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 31 Sayı: 3
  • Basım Tarihi: 2007
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.0-326
  • Anahtar Kelimeler: acyl hydrazone, 1,2,4-triazole, 1,3,4-oxadiazole, Schiff base, reduction, acetylation, antimicrobial, activity, antifungal activity, AROMATASE INHIBITORS, ANTIBACTERIAL
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

A series of acylhydrazones (2a-d) was synthesized from the reactions of iminoester hydrochlorides (la-e) with acyl hydrazines. 2,5-Dialkyl 1,3,4-oxadiazoles (3a-d) were obtained in the same reaction media. The treatment of acylhydrazones with hydrazine hydrate afforded 4-amino-3,5-dialkyl-1,2,4-triazoles (4a-c). The acetylation of 4-amino-3-(4-hydroxyphenyl)-5-phenyl-4H-1,2,4-triazole (4a) produced 4-amino-5-(4-acetoxyphenyl)-3-phenyl-4H-.1,2,4-triazole (9), while the acetylation of 4-amino-3-(4-tolyl)-5-phenyl-4H-1,2,4-triazole (4b) gave 4.-acetylamino-3-phenyl-5-(4-tolyl)-4H-1,2,4-triazole (10). The treatment of compound 4b with various aromatic aldehydes or acetophenone and 4-nitroacetophenone resulted in the formation of 4-arylidenamino-3,5-dialkyl-4H-1,2,4-triazoles (5a-e and 7a,b). Sodium borohydride reduction of 4-arylidenamino derivatives of 1,2,4-triazoles afforded 4-alkyl amino-3,5-dialkyl-4H-1,2,4-triazoles (6a-e and 8a,b).