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Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile.

ABSTRACT: The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2'-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2?,3?:2',3']pyrrolo[3',4':4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chloride, isatins and ethyl cyanoacetate mainly resulted in functionalized spiro[indoline-3,8'-pyrido[2',3':4,5]pyrrolo[2,1-a]isoquinolines].

SUBMITTER: Sun J

PROVIDER: S-EPMC5247726 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile.

Sun Jing J Shen Guo-Liang GL Huang Ying Y Yan Chao-Guo CG

Scientific reports 20170120

The triethylamine promoted three-component reaction of N-(4-nitrobenzyl), N-ethoxycarbonylmethylisoquinolinium bromide, isatins and malononitrile in ethanol afforded spiro[indoline-3,2'-pyrrolo[2,1-a]isoquinolines] in good yields and with high diastereoselectivity. The similar reaction of N-cyanomethylisoquinolinium chloride mainly gave complex indolo[2″,3″:2',3']pyrrolo[3',4':4,5]pyrrolo[2,1-a]isoquinoline derivatives. However, the three-component reaction of N-cyanomethylisoquinolinium chlorid ...[more]

PMID: 28106130

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