Advances in the synthesis and chemical transformations of 5-acetyl-1,3,4-thiadiazolines

ABSTRACT

5-Acetyl-1,3,4-thiadiazolines are a versatile class of heterocycles which find wide application in medicinal and materials chemistry. The objective of this review is to describe the different strategies developed so far for the synthesis of 5-acetyl-1,3,4-thiadiazolines and their analogues as well as to highlight their reactivity in the synthesis of chemically relevant bioactive heterocyclic compounds. The first part of this review describes the diverse synthetic approaches to synthesize 5-acetyl-1,3,4-thiadiazolines based on the [4π + 2π] cycloaddition reaction of C-acetyl nitrile imines with reagents having sulfur diploarphiles. The synthetic methods have been organized on the basis of the type of sulfur reagent employed in the syntheses. In the second part, an overview of the transformations of 5-acetyl-1,3,4-thiazolines into heterocyclic compounds such as pyrazoles, thiazoles, 1,3,4-thiadiazoles, imidazoles, pyridines, and pyrimidines as well as other relevant condensed derivatives, is presented.

GRAPHICAL ABSTRACT

KEYWORDS:

• 5-acetylthiadiazolines
• hydrazonoyl halides
• thioamides
• isothiocyanates
• thiazoles
• pyridines
• pyrimidines

Disclosure statement

No potential conflict of interest was reported by the author(s).