Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines

[Image: see text] The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent...

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Autores principales: Kolarski, Dušan, Szymanski, Wiktor, Feringa, Ben L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633830/
https://www.ncbi.nlm.nih.gov/pubmed/28891651
http://dx.doi.org/10.1021/acs.orglett.7b02361
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author Kolarski, Dušan
Szymanski, Wiktor
Feringa, Ben L.
author_facet Kolarski, Dušan
Szymanski, Wiktor
Feringa, Ben L.
author_sort Kolarski, Dušan
collection PubMed
description [Image: see text] The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent yields. Photophysical studies revealed intensive n−π* absorption band that makes trans-to-cis photoswitching possible using visible light (λ = 530 nm).
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spelling pubmed-56338302017-10-11 Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines Kolarski, Dušan Szymanski, Wiktor Feringa, Ben L. Org Lett [Image: see text] The first general two-step, one-pot synthetic route to 6-azopurines is presented. Microwave-assisted nucleophilic aromatic substitution of protected 6-chloropurines with hydrazines or hydrazides, followed by metal-free oxidation with oxygen, gives 6-azopurines in high to excellent yields. Photophysical studies revealed intensive n−π* absorption band that makes trans-to-cis photoswitching possible using visible light (λ = 530 nm). American Chemical Society 2017-09-11 2017-10-06 /pmc/articles/PMC5633830/ /pubmed/28891651 http://dx.doi.org/10.1021/acs.orglett.7b02361 Text en Copyright © 2017 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Kolarski, Dušan
Szymanski, Wiktor
Feringa, Ben L.
Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title_full Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title_fullStr Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title_full_unstemmed Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title_short Two-Step, One-Pot Synthesis of Visible-Light-Responsive 6-Azopurines
title_sort two-step, one-pot synthesis of visible-light-responsive 6-azopurines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5633830/
https://www.ncbi.nlm.nih.gov/pubmed/28891651
http://dx.doi.org/10.1021/acs.orglett.7b02361
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