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Asian Journal of Organic Chemistry · 2023 ·Vol. 12 ·期 5 ·e202300015 · IF 2.7

Transition-Metal-Free α-C-Alkylation of Oxindoles with Alcohols

Yu-Tong Duan,Zhong-Xia Wang

Graphical Transition-metal-free reaction of oxindoles with primary or secondary alcohols in the presence of LiO t Bu affords α-C-alkylated oxindoles. Transition-metal-free α-C-alkylation of oxindoles with alcohols was performed. The reaction requires the presence of LiO t Bu and proceeds under thermal conditions. The method exhibits a wide scope of substrates. Both primary and secondary aliphatic and aromatic alcohols can be employed as the alkylating reagents. Oxindole and various 1-alkyl- or 1-aryl-substituted oxindoles can be alkylated. The mechanistic studies show that the reaction may involve both free radical and aldol condensation/MPV processes.

CAS / MDL: 64-17-5 61-70-1 59-48-3

研究领域: 有机化学 · 合成化学

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TETRAHEDRON · 2017 · IF 2.651

3-Methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles for synthesis of polycyclic 3,3′-pyrrolidinyl-dispirooxindoles and their biological evaluation for anticancer activities

Bing Lin,Wen-Hui Zhang,Dan-Dan Wang,Yi Gong,Qi-Di Wei,Xiong-Li Liu,Ting-Ting Feng,Ying Zhou,Wei-Cheng Yuan

Developed herein is a diversity-oriented one-pot multicomponent synthesis of polycyclic 3,3′- pyrrolidinyl-dispirooxindoles 3 via a multicomponent 1,3-dipolar cycloaddition event of 3-methyl-4-nitro-5-isatylidenyl-isoxazoles 2 with azomethine ylides (thermally generated in situ from isatins and proline or thioproline). Products bearing four consecutive stereocenters consist of two oxindole moieties and a polycyclic pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 85% yield) with good diastereoselectivity (up to >20:1). Valuable features of this method were application of 3-methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles and the design of new hybrid architectures for biological screenings through the adequate fusion of these sub-units of isoxazole and 3,3′-pyrrolidinyl-dispirooxindole, generating drug-like molecules.

CAS / MDL: 14913-33-8

研究领域: 有机化学 · 药物化学 · 肿瘤学

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TETRAHEDRON · 2017 · IF 2.651

Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles

Ling-Ling Wu,Gao H. Yang,Zhi Guan,Yan-Hong He

The Rose Bengal sensitized intermolecular [2 + 2]-cycloaddition of 3-ylideneoxindoles for the synthesis of spirocyclic oxindoles was developed successfully under visible light irradiation conditions. The cycloaddition products were obtained in good yields (up to 93%) with excellent diastereoselectivity and regioselectivity by using a low loading of Rose Bengal (0.125 mol%) as a triplet sensitizer. This work demonstrates the potential benefits of Rose Bengal in visible light catalysis.

CAS / MDL: 632-69-9

研究领域: 有机化学 · 光化学

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Transition-Metal-Free α-C-Alkylation of Oxindoles with Alcohols

3-Methyl-4-nitro-5-isatylidenyl-isoxazoles as 1,3-dipolarophiles for synthesis of polycyclic 3,3′-pyrrolidinyl-dispirooxindoles and their biological evaluation for anticancer activities

Metal-free visible-light-promoted intermolecular [2+2]-cycloaddition of 3-ylideneoxindoles