Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch

[Image: see text] Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger t...

Descripción completa

Detalles Bibliográficos
Autores principales: Ciccolini, Cecilia, Mari, Giacomo, Gatti, Francesco G., Gatti, Giuseppe, Giorgi, Gianluca, Mantellini, Fabio, Favi, Gianfranco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8010796/
https://www.ncbi.nlm.nih.gov/pubmed/32786612
http://dx.doi.org/10.1021/acs.joc.0c01489
_version_ 1783673128193359872
author Ciccolini, Cecilia
Mari, Giacomo
Gatti, Francesco G.
Gatti, Giuseppe
Giorgi, Gianluca
Mantellini, Fabio
Favi, Gianfranco
author_facet Ciccolini, Cecilia
Mari, Giacomo
Gatti, Francesco G.
Gatti, Giuseppe
Giorgi, Gianluca
Mantellini, Fabio
Favi, Gianfranco
author_sort Ciccolini, Cecilia
collection PubMed
description [Image: see text] Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.
format Online
Article
Text
id pubmed-8010796
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-80107962021-03-31 Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch Ciccolini, Cecilia Mari, Giacomo Gatti, Francesco G. Gatti, Giuseppe Giorgi, Gianluca Mantellini, Fabio Favi, Gianfranco J Org Chem [Image: see text] Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations. American Chemical Society 2020-08-12 2020-09-04 /pmc/articles/PMC8010796/ /pubmed/32786612 http://dx.doi.org/10.1021/acs.joc.0c01489 Text en Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ciccolini, Cecilia
Mari, Giacomo
Gatti, Francesco G.
Gatti, Giuseppe
Giorgi, Gianluca
Mantellini, Fabio
Favi, Gianfranco
Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title_full Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title_fullStr Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title_full_unstemmed Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title_short Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
title_sort synthesis of polycyclic fused indoline scaffolds through a substrate-guided reactivity switch
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8010796/
https://www.ncbi.nlm.nih.gov/pubmed/32786612
http://dx.doi.org/10.1021/acs.joc.0c01489
work_keys_str_mv AT ciccolinicecilia synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT marigiacomo synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT gattifrancescog synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT gattigiuseppe synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT giorgigianluca synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT mantellinifabio synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch
AT favigianfranco synthesisofpolycyclicfusedindolinescaffoldsthroughasubstrateguidedreactivityswitch

Ejemplares similares