N-Methylpyridinium Tosylate Catalysed Green Synthesis, X-Ray Studies and Antimicrobial Activities of Novel (E)-3-Amino-2-(e)-(3, 4-Dihydronaphthalen-1(2H)-Ylidene)Hydrazono)Thiazolidin-4-Ones

Abstract

3,4-Dihydro-2H-naphthalen-1-ones 1,on reaction with thiocarbohydrazide, afforded monothiocarbohydrazones 2, which, on condensation with chloroacetic acid in the presence of an ionic liquid and bromotrimethylsilane furnish (E)-3-amino-2-(E)-(3,4-dihydronaphthalen-1-(2H)-ylidene)hydrazono)thiazolidin-4-ones 3 in quantitative yields. Acetyl derivatives 5 were obtained from 3 with acetic anhydride. Monothiocarbohydrazones 2 on condensation with benzaldehyde yield azomethines 4. The structure of compounds 2–5 has been established by elemental analysis, IR, ¹H NMR, and mass spectral data. The structure of compound 3a has been further confirmed by X-ray crystallographic data. The compounds 2–5 were screened for antimicrobial activity. The thiazolidinones 3a and 3b showed maximum antimicrobial activities.

GRAPHICAL ABSTRACT

Keywords:

• Monothiocarbohydrazones
• 4-thiazolidinones
• spectral data
• X-ray crystallographic data

Acknowledgments

One of the authors Richa Gupta is thankful to the authorities of Sant Longowal Institute of Engineering and Technology, Longowal for providing financial assistance. The facilities provided by SLIET authorities are gratefully acknowledged.

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