Synthesis of novel series of 3,5-disubstituted imidazo[1,2-d] [1,2,4]thiadiazoles involving S_NAr and Suzuki–Miyaura cross-coupling reactions

Abstract

A convenient design of 3,5-disubstituted imidazo[1,2-d][1,2,4]thiadiazoles is reported from 2-mercaptoimidazole, which afforded a versatile platform that was then used to access a variety of original heterocycles.

Access to Mono‐, Di‐ and Tri‐(Het)Arylated Pyrazolo[5,1‐b]oxazoles Using Cyclization, C−H Activation and Suzuki–Miyaura Palladium‐Catalyzed Reactions

“…In order to examine the reactivity in C-7 position, we conducted a selective halogenation with N-iodosuccinimide in DMF at r. t. which was performed on a representative panel of 7) with a satisfactory efficiency. [40] With these halogenated derivatives in hand, iodine displacement was achieved by Suzuki-Miyaura cross-coupling and gave access also to C-7 substituted pyrazolo[5,1-b]oxazoles of type I. This objective prompted us to find a general and efficient catalytic system by optimizing the main reaction parameters.…”

“…In order to examine the reactivity in C ‐7 position, we conducted a selective halogenation with N‐ iodosuccinimide in DMF at r. t. which was performed on a representative panel of disubstituted pyrazolo[5,1‐ b ]oxazoles of type I to afford derivatives 47 – 51 (Table 7) with a satisfactory efficiency [40] …”

N‐Substituted piperazine‐coupled imidazo[2,1‐b]thiazoles as inhibitors of Mycobacterium tuberculosis: Synthesis, evaluation, and docking studies

“…In the field of medical chemistry, fused heterobicyclic molecules have become increasingly significant. On such fused heterobicyclic unit, imidazo[2,1‐ b ]thiazole has a significant place in medicinal chemistry due to their extensive spectrum of physiological actions (Leoni et al, 2017; Pescheteau et al, 2022). The primary chemical component of the immunostimulatory and anthelminthic medication levamisole, also known by the brand name Ergamisol, is imidazo[2,1‐ b ]thiazole (Fenichel & Chirigos, 1984; Shareef et al, 2020).…”

Synthesis and antiviral activity of novel imidazo[2,1‐b]thiazoles coupled with morpholine and thiomorpholines

“…Synthesis and antiviral activity of novel imidazo[2,1-b]thiazoles coupled with morpholine and thiomorpholines (7a-l). Imidazo[2,1-b]thiazole derivatives are biologically active and play an important role in medicinal chemistry due to their wide range of physiological activities [16,17]. In recent years, these scaffolds have been used against various diseases and disorders such as anticancer [18], antiviral [19], antitubercular [20], antioxidant [21], and anti-inflammatory [22].…”