Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone

作者：Peng, Chuqin; Ren, Jiwei; Xiao, Jun-An; Zhang, Honggang; Yang, Hua^*; Luo, Yiming

来源：Beilstein Journal of Organic Chemistry, 2014, 10: 352-360.

DOI：10.3762/bjoc.10.33

• 1,3-dipolar cycloaddition
• azomethine ylide
• regioselectivity
• spirooxindole

1,3-Dipolar cycloadditions of isatins, benzylamine and benzylideneacetones were studied to prepare a series of novel spiropyrrolidine-oxindoles - 4'-acetyl-3',5'-diarylspiro[indoline-3,2'-pyrrolidin]-2-ones and 3'-acetyl-4',5'-diarylspiro[indoline-3,2'-pyrrolidine]-2-ones in good yields of up to 94% and with good regioselectivities. Regioselectivities are reversible by the addition of water or 4-nitrobenzoic acid, respectively. The substituent effects on the regioselectivity were also investigated.

• 出版日期2014-2-7
• 单位中南大学