Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles

ABSTRACT: The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1[Formula: see text] -quinolizines] in high yields and with high diastereoselectivity. The Diels–Alder reactions of spiro[indoline-3,1[Formula: s...

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Detalles Bibliográficos
Autores principales: Sun, Jing, Gong, Hui, Sun, Yan, Yan, Chao-Guo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Netherlands 2013
Materias:
Full-Length Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3836201/
https://www.ncbi.nlm.nih.gov/pubmed/23868182
http://dx.doi.org/10.1007/s11030-013-9459-5
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author Sun, Jing
Gong, Hui
Sun, Yan
Yan, Chao-Guo
author_facet Sun, Jing
Gong, Hui
Sun, Yan
Yan, Chao-Guo
author_sort Sun, Jing
collection PubMed
description ABSTRACT: The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1[Formula: see text] -quinolizines] in high yields and with high diastereoselectivity. The Diels–Alder reactions of spiro[indoline-3,1[Formula: see text] -quinolizines] with maleic anhydride and [Formula: see text] -phenyl maleimides successfully resulted in polyfunctionalized isoquinolinuclidine derivatives. The similar three-component reactions with quinoline resulted in the novel spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] in moderate to good yields. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s11030-013-9459-5) contains supplementary material, which is available to authorized users.
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spelling pubmed-38362012013-11-22 Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles Sun, Jing Gong, Hui Sun, Yan Yan, Chao-Guo Mol Divers Full-Length Paper ABSTRACT: The three-component reactions of substituted pyridines, dimethyl acetylenedicarboxylates, and 3-phenacylideneoxindoles afforded spiro[indoline-3,1[Formula: see text] -quinolizines] in high yields and with high diastereoselectivity. The Diels–Alder reactions of spiro[indoline-3,1[Formula: see text] -quinolizines] with maleic anhydride and [Formula: see text] -phenyl maleimides successfully resulted in polyfunctionalized isoquinolinuclidine derivatives. The similar three-component reactions with quinoline resulted in the novel spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] in moderate to good yields. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s11030-013-9459-5) contains supplementary material, which is available to authorized users. Springer Netherlands 2013-07-19 2013 /pmc/articles/PMC3836201/ /pubmed/23868182 http://dx.doi.org/10.1007/s11030-013-9459-5 Text en © The Author(s) 2013 https://creativecommons.org/licenses/by/2.0/ Open AccessThis article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited.
spellingShingle Full-Length Paper
Sun, Jing
Gong, Hui
Sun, Yan
Yan, Chao-Guo
Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title_full Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title_fullStr Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title_full_unstemmed Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title_short Synthesis of spiro[indoline-3,1[Formula: see text] -quinolizines] and spiro[indoline-3,4[Formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
title_sort synthesis of spiro[indoline-3,1[formula: see text] -quinolizines] and spiro[indoline-3,4[formula: see text] -pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles
topic Full-Length Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3836201/
https://www.ncbi.nlm.nih.gov/pubmed/23868182
http://dx.doi.org/10.1007/s11030-013-9459-5
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