Heterocyclization of acylthiosemicarbazides

Abstract

The review summarizes published data on the behavior and reactions of acylthiosemicarbazides and their derivatives, which lead to the formation of heterocyclic systems, including methods of preparation in addition to synthesis of pyrrole, thiazole, thiadiazole, thiadiazolidine, and triazole derivatives as well as fused heterocyclic compounds.

1,2-Dibenzoylthiosemicarbazide

“…1,4-Dibenzoylthiosemicarbazide (4) was obtained from benzoylhydrazine (7) and benzoyl isothiocyanate (8), according to a method from the literature [15]. White crystalline powder (η = 67%), m.p.…”

“…1-Acylthiosemicarbazides are used in the preparation of heterocyclic compounds [8,9], but the literature reports few details on the acylation reaction as follows:…”

Antiproliferative Activity and Ultrastructural Changes in Promastigote and Amastigote forms of Leishmania amazonensis Caused by Limonene‐Acylthiosemicarbazide Hybrids

“…Acylthiosemicarbazides are a subclass of thiosemicarbazides with a carbonyl group attached to position N‐1 (Figure 1). These compounds can be synthesized by reactions that involve the addition of hydrazines to isothiocyanates and the condensation of thiosemicarbazides with esters or substituted acid chloride [24] . In addition, acylthiosemicarbazides are widely employed as strategic synthetic intermediates for preparing several nitrogen‐containing five‐membered heterocycles as 1,3,4‐thiadiazoles, 1,3,4‐oxadiazoles and 1,2,4‐triazoles [25,26] and metal complexes [27]…”

“…These compounds can be synthesized by reactions that involve the addition of hydrazines to isothiocyanates and the condensation of thiosemicarbazides with esters or substituted acid chloride. [24] In addition, acylthiosemicarbazides are widely employed as strategic synthetic intermediates for preparing several nitrogencontaining five-membered heterocycles as 1,3,4-thiadiazoles, 1,3,4-oxadiazoles and 1,2,4-triazoles [25,26] and metal complexes. [27] Acylthiosemicarbazides derivatives also have exhibited a broad spectrum of pharmacological properties as antimicrobial, anti-inflammatory [28,29] and antitumor.…”

Thiosemicarbazide Derivatives as Building Block in Synthesis of Target Heterocyclic Compounds with Their Antimicrobial Assessment

“…Acylhydrazone moieties are important pharmacophoric cores of several anti‐inflammatory, anti‐nociceptive, and anti‐platelet activities . Thiosemicarbazides are valuable building blocks for the synthesis of different heterocyclic ring systems . Their synthesis includes several methods , and the method most frequently used is the reactions of isothiocyanates with hydrazines .…”