1076-59-1Relevant articles and documents
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Hydorn,A.E. et al.
, p. 4305 - 4309 (1962)
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Palladium catalyzed insertion reaction of isocyanides with 3-arylisoxazol-5(4 H)-ones: Synthesis of 4-aminomethylidene isoxazolone derivates
Zhu, Yi-Ming,Xu, Pei,Wang, Shun-Yi,Ji, Shun-Jun
, p. 11007 - 11013 (2019)
A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4H)-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C-H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.
Organocatalytic Enantioselective 1,6-aza-Michael Addition of Isoxazolin-5-ones to p-Quinone Methides
Torán, Ricardo,Vila, Carlos,Sanz-Marco, Amparo,Mu?oz, M. Carmen,Pedro, José R.,Blay, Gonzalo
, p. 627 - 630 (2020)
A thiourea-Br?nsted base bifunctional catalyst allowed the enantioselective 1,6-aza-Michael addition of isoxazolin-5-ones to p-quinone methides to give isoxazolin-5-ones having a chiral diarylmethyl moiety attached to the N atom with fair to good yields and enantiomeric excesses. To the best of our knowledge this reaction represents the first example of enantioselective N-alkylation of isoxazolin-5-ones as well as the first example of enantioselective 1,6-aza-Michael reaction involving p-quinone methides.
The tyrosinase inhibitory effects of isoxazolone derivatives with a (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold
Kim, Su Jeong,Yang, Jungho,Lee, Sanggwon,Park, Chaeun,Kang, Dongwan,Akter, Jinia,Ullah, Sultan,Kim, Yeon-Jeong,Chun, Pusoon,Moon, Hyung Ryong
, p. 3882 - 3889 (2018)
Thirteen (Z)-4-(substituted benzylidene)-3-phenylisoxazol-5(4H)-ones were designed to confirm the geometric effect of the double bond of the β-phenyl-α, β-unsaturated carbonyl scaffold on tyrosinase inhibitory activity. Compounds 1a–1m, which all possessed the (Z)-β-phenyl-α, β-unsaturated carbonyl scaffold, were synthesized using a tandem reaction consisting of an isoxazolone ring formation and a Knoevenagel condensation, and three starting materials, ethyl benzoylacetate, hydroxylamine and benzaldehydes. Some of the compounds showed inhibitory activity against mushroom tyrosinase as potent as compounds containing the “(E)”-β-phenyl-α, β-unsaturated carbonyl scaffold. Compounds 1c and 1m showed greater inhibitory activity than kojic acid: IC50 = 32.08 ± 2.25 μM for 1c; IC50 = 14.62 ± 1.38 μM for 1m; and IC50 = 37.86 ± 2.21 μM for kojic acid. A kinetic study indicated that 1m inhibited tyrosinase in a competitive manner and that it probably binds to the enzyme's active site. In silico docking simulation supported binding of 1m (?7.6 kcal/mol) to the active site of tyrosinase with stronger affinity than kojic acid (?5.7 kcal/mol). Similar results were obtained using cell-based assays, and in B16F10 cells, compound 1m dose-dependently inhibited tyrosinase activity and melanogenesis. These results indicate the anti-melanogenic effect of compound 1m is due to the inhibition of tyrosinase and (Z)-isomer of the β-phenyl-α, β-unsaturated carbonyl scaffold can, like its congener the (E)-isomer, act as an excellent scaffold for tyrosinase inhibition.
A synthetic route towards 3,4-disubstituted pyrrolidin-2-ones: via a Michael addition and reductive ring closing strategy
Dawange, Monali,Parekh, Nikita,Kumbhar, Avinash,Dehaen, Wim,Kusurkar, Radhika
, p. 3612 - 3618 (2017)
Pyrrolidin-2-one derivatives were synthesized via DABCO mediated Michael addition of isoxazol-5(4H)-ones with nitroalkenes, followed by one pot reduction of the nitro group and ring cleavage with cyclization. 2-Pyrrolidinone scaffolds with a wide range of substituents were synthesized with good yield and diastereoselectivity by using this protocol.
Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones
Hu, Wangcheng,He, Xinwei,Zhou, Tongtong,Zuo, Youpeng,Zhang, Shiwen,Yang, Tingting,Shang, Yongjia
, p. 552 - 556 (2021/02/06)
A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.