Synthesis of Diastereoenriched α‐Aminomethyl Enaminones via a Brønsted Acid‐Catalyzed Asymmetric aza‐Baylis‐Hillman Reaction of Chiral N‐Phosphonyl Imines

Abstract

An effective chiral GAP methodology for preparing α‐aminomethyl enaminones through a (R)‐CSA‐catalyzed asymmetric aza‐Baylis‐Hillman reaction is reported. Excellent yields and high diastereoselectivity could be obtained under mild conditions and convenient GAP techniques. The confirmations of the absolute configuration of N‐phosphonyl imine and chiral enaminone by X‐ray diffraction provides an explicit explanation of the chirality mechanism for GAP chemistry.

Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI‐Fe3O4@SiO2 (TMS‐EDTA)

“…[ 26 ] Furthermore, it has been found that two 2‐(2,4‐dimethoxy phenylamino)‐5 methylene‐4‐thiazolinone derivatives ( B in Figure 1) with IC 50 values of 34.1 and 52.6 μM were effective tyrosinase inhibitors. [ 25 ] Our previous study indicated that two phthalimide‐1,2,3‐trizole hybrid compounds ( C in Figure 1) showed less inhibitory activity on tyrosinase ((IC 50 s = 26.2 and 26.5 μM) than the reference drug kojic acid did. [ 24 ] Moreover, it was proved that benzimidazole‐1,2,3‐triazole hybrid compounds ( D in Figure 1) exhibited effective inhibitory activity comparable to that of kojic acid with IC 50 values of 9.42 and 10.34 μM which were comparable to that of kojic acid (IC 50 = 9.28 μM).…”

“…1,2,3–Triazole and thiazolone scaffolds have shown various biological activities including; antitumors, [ 1,2 ] anti‐HIV, [ 3 ] anti‐allergy, [ 4 ] antifungal, [ 5–7 ] anti‐infection, [ 8,9 ] anticancer, [ 10 ] antiviral, [ 11–13 ] and antimicrobial properties. [ 14–22 ] Furthermore, the regioselectivity of cycloadducts is crucial [ 23–26 ] and it has been found that some 1,2,3‐triazole and thiazolone derivatives exhibited antityrosinase activity. [ 23–26 ] Tyrosinase, also known as polyphenol oxidase, is a copper‐containing enzyme abundantly distributed in nature.…”

“…[ 14–22 ] Furthermore, the regioselectivity of cycloadducts is crucial [ 23–26 ] and it has been found that some 1,2,3‐triazole and thiazolone derivatives exhibited antityrosinase activity. [ 23–26 ] Tyrosinase, also known as polyphenol oxidase, is a copper‐containing enzyme abundantly distributed in nature. This enzyme participates in the biosynthesis of melanin by catalyzing the hydroxylation of L‐tyrosine to 3,4‐dihydroxyphenylalanine, L‐DOPA (mycophenolate activity) and subsequently, oxidation of L‐DOPA to dopaquinone (diphenolase activity).…”

An experimental and mechanism study on the regioselective click reaction toward the synthesis of thiazolidinone-triazole

“…One of the most efficient synthetic tools for triazole derivatives' convenient preparation in a regioselective manner is the click reaction [1,2]. Click reaction proceeds with regioselectivity and has an optimal atom economy, which is influential and crucial in synthetic chemistry [3,4]. 1,2,3-Triazole scaffolds are utilized for treatment of HIV [5], tumors [6,7] allergy [8], fungal infection [9,10] and microbial diseases [11,12,13,14,15].…”

Acenaphtoquinoxaline as a selective fluorescent sensor for Hg (II) detection: experimental and theoretical studies

“…Thus, the development of novel, highly sensitive, and selective chemosensors for the convenient and rapid detection of metal ions is considerably increased. The design and synthesis of highly selective sensors for metal ion in the aqueous or non-aqueous media have been received much attention as an active area of research, exclusively, fluorescent sensors are a rapidly developing field of research [25,26,27,28,29,30], which have gained significant attention because of their exciting features as high reversibility, specificity, and sensitivity [31,32]. A chemosensor fluorophore is immensely demanded in terms of economic viewpoint [33,34,35].…”