Divergent Approach to Thiazolylidene Derivatives: A Perspective on the Synthesis of a Heterocyclic Skeleton from β-Amidothioamides Reactivity

Abstract

Herein we report a domino protocol able to reach regioselectively thiazolylidene systems by combining the reactive peculiarities of both β-amidothioamides (ATAs) and 1,2-diaza-1,3-dienes (DDs). Depending on the reaction conditions and/or the nature of the residue at C4 of the heterodiene system, ATAs can act as hetero-mononucleophiles or hetero-dinucleophiles in the diversified thiazolylidene ring assembly.

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

“…Santeusanio et al [66] reported a domino reaction, also known as a cascade reaction, consisting of at least two subsequent reactions where segregation of the intermediate is not required and occurs intramolecularly with advantages like less waste generation, fast reaction and high atom economy. In the multifarious thiazolylidene ring congregation, ATAs (β-amidothioamides) can act as heteromononucleophiles or heterodinucleophiles.…”

“…Modified from Ref. [66] Yahiaoui and coauthors [68] described a reliable and simple protocol for the preparation of 2-thioxo-thiazolidin-4-ones 28 by condensation of aromatic amines and CS 2 using NH 4 OH and chloroacetic acid, and the compounds were further treated with CH 3 CN under basic conditions (Scheme 13). The authors also developed a combined experimental and theoretical approach on the molecular struc-…”

“…Nanjan et al [57] reviewed the antidiabetic activity of thiazolidinone. But there is no detailed review of the synthesis and biological activity of 4 Comparative study of various synthetic protocols [58][59][60][61][62][63][64][65][66][67][68][69] Fig. 5 Comparative study of various synthetic protocols [77][78][79][80][81][82][83][84][85][86] Topics in Current Chemistry (2020) 378:34 1 3 34 Page 8 of 90 hoping to inspire new and even more creative approaches for researchers ( Fig.…”

One-Pot Synthesis of Novel 2-Imino-5-Arylidine-Thiazolidine Analogues and Evaluation of Their Anti-Proliferative Activity against MCF7 Breast Cancer Cell Line

“…Therefore, thiazolidines exhibit a broad array of medicinal applications, which have inspired researchers to develop novel methodologies for their synthesis. Acid- and base-catalyzed thiazolidine syntheses have been reported as approaches to these heterocycles however, most of these synthetic methods require elevated temperatures and long reaction times and are characterized by low yields and moderate substrate scope [ 25 , 26 , 27 , 28 , 29 ]. In addition, ionic-liquid-assisted synthesis of thiazolidine is considered to be an efficient method but in some cases requires introduction of additional catalysts; otherwise, yields can be an issue [ 30 ].…”

Participation of β-Ketothioamides in N-Heterocyclic Carbene-Catalyzed [3 + 3] Spiroannulation: Asymmetric Synthesis of Functionalized Spiro-piperidinone Derivatives

“…Over the past decade, β-ketothioamides (KTAs) acting as versatile synthons have received considerable attention and experienced very rapid development . Having multiple active centers, KTAs are used not only as dinucleophilic reagents (Figure , types A–C) but also as dielectrophilic reagents in numerous reactions (Figure , type D), displaying a powerful ability for the construction of functionalized heterocyclic compounds . Although intensive research efforts have been made in KTA chemistry, to date, the asymmetric reactions based on KTAs are still very rare with only few examples reported .…”