Utility involving thioacetoacetanilides as precursors for synthesis of new thiazole, thiadiazole and thiophene derivatives with antimicrobial activity

ABSTRACT

The behavior of thioacetoacetanilide (1) and/or α-arylhydrazono-thioacetoacetanilides 4 toward many different α-halocarbonyl compounds was demonstrated. Thus, reactions of 1 with α-bromoketones (bromoacetone and phenacyl bromide) and hydrazonoyl bromides afforded the corresponding thiazole, thiophene and 1,3,4-thiadiazole derivatives, respectively. The synthesis and reactivity of thiazolidin-5-one 2 toward aromatic diazonium chlorides and aromatic aldehydes were described. Most of the synthesized compounds were screened for their antibacterial and antifungal activities and showed accepted antimicrobial activities with respect to the control drugs.

GRAPHICAL ABSTRACT

KEYWORDS:

• Phenyl isothiocyanate
• thioacetoacetanilide
• phenacyl bromide
• thiazolidin-5-one
• diazonium chloride
• thiadiazole
• thiophene

Disclosure statement

No potential conflict of interest was reported by the authors.

ORCID

Ahmed Fekri http://orcid.org/0000-0001-9733-1161