Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

Abstract

An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80°C in DMSO medium. A plausible mechanism is proposed in which a-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

“…Based on the results of our experiments and previous literature, [18][19][20][21][22][23][24][25] we propose the following reaction pathway (Scheme 1). Briefly, acetophenone (1a) is converted into α-iodoketone A in the presence of the I 2 catalyst.…”

“…18 Subsequently, various modified Hantzsch methods have been developed such as using heterogeneous catalysts, microwave heating, solid synthesis, or greener solvents including ionic liquids, PEG-400, and water. [19][20][21][22][23][24][25] Other synthetic methods toward 2-aminothiazoles have utilized different coupling partners such as phenyl thiocyanates and propargylamines, alkyne(alkene)-substituted iodine(III) reagents and thioureas, 1,2-dicyano-3-bromo-2-phenylpropenes and thioureas, and α-SCN-substituted ketones and amines. [26][27][28][29] However, the preparation of these coupling materials is generally difficult, needing multiple steps and harsh reaction conditions.…”

Multicomponent Reactions Promoted by Ecocatalyst from Metal Hyperaccumulating Plant Pluchea sagittalis

“…The porosity presented by Cat C mainly results from its interparticle porosity (Figure 7c). Then, Cat B presents a substantially higher specific surface area (Table 5) that is a consequence of the presence of the MK10 clay, a well-known and catalytically applied layered aluminosilicate [76,77], which was added during the synthesis of Cat B and possesses a superficial area close to 250 m 2 g −1 [78]. Consequently, over the specific surface area of the MK10 clay, the lower amount of the supported catalytically active metallic species is highly dispersed, a behavior that was confirmed by its XRD diffractogram (Figure 3), which does not show metallic oxide diffraction peaks.…”

The untold story of starch as a catalyst for organic reactions

“…Structures containing 2-aminothiazole moiety are an important class in the family of heterocyclic compounds and have many potential applications especially in medicinal chemistry because of their anti-cancer and anti-tumor, anti-viral, anti-inammatory, and antimicrobial activities. [53][54][55] Moreover, these compounds can be used as convenient substrates to prepare more complex products like corresponding azo derivatives 56 and many polycyclic heterocyclic compounds. 57,58 In 2017, our team at the University of Kashan found that simple starch can promote the synthesis of 2-aminothiazole derivatives in the presence of molecular iodine as a halogenating agent (Scheme 2).…”