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

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-cyanomet...

Descripción completa

Detalles Bibliográficos
Autores principales: Sun, Jing, Shen, Guo-liang, Huang, Ying, Yan, Chao-Guo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5247726/
https://www.ncbi.nlm.nih.gov/pubmed/28106130
http://dx.doi.org/10.1038/srep41024
_version_ 1782497129373106176
author Sun, Jing
Shen, Guo-liang
Huang, Ying
Yan, Chao-Guo
author_facet Sun, Jing
Shen, Guo-liang
Huang, Ying
Yan, Chao-Guo
author_sort Sun, Jing
collection PubMed
description 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].
format Online
Article
Text
id pubmed-5247726
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher Nature Publishing Group
record_format MEDLINE/PubMed
spelling pubmed-52477262017-01-23 Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile Sun, Jing Shen, Guo-liang Huang, Ying Yan, Chao-Guo Sci Rep Article 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]. Nature Publishing Group 2017-01-20 /pmc/articles/PMC5247726/ /pubmed/28106130 http://dx.doi.org/10.1038/srep41024 Text en Copyright © 2017, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Sun, Jing
Shen, Guo-liang
Huang, Ying
Yan, Chao-Guo
Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title_full Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title_fullStr Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title_full_unstemmed Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title_short Formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
title_sort formation of diverse polycyclic spirooxindoles via three-component reaction of isoquinolinium salts, isatins and malononitrile
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5247726/
https://www.ncbi.nlm.nih.gov/pubmed/28106130
http://dx.doi.org/10.1038/srep41024
work_keys_str_mv AT sunjing formationofdiversepolycyclicspirooxindolesviathreecomponentreactionofisoquinoliniumsaltsisatinsandmalononitrile
AT shenguoliang formationofdiversepolycyclicspirooxindolesviathreecomponentreactionofisoquinoliniumsaltsisatinsandmalononitrile
AT huangying formationofdiversepolycyclicspirooxindolesviathreecomponentreactionofisoquinoliniumsaltsisatinsandmalononitrile
AT yanchaoguo formationofdiversepolycyclicspirooxindolesviathreecomponentreactionofisoquinoliniumsaltsisatinsandmalononitrile

Ejemplares similares