Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis

Prebiotically plausible ferrocyanide–ferricyanide photoredox cycling oxidatively converts thiourea to cyanamide, whilst HCN is reductively homologated to intermediates which either react directly with the cyanamide giving 2-aminoazoles, or have the potential to do so upon loss of HCN from the system...

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Detalles Bibliográficos
Autores principales: Liu, Ziwei, Wu, Long-Fei, Bond, Andrew D., Sutherland, John D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7808312/
https://www.ncbi.nlm.nih.gov/pubmed/33151212
http://dx.doi.org/10.1039/d0cc05752e
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author Liu, Ziwei
Wu, Long-Fei
Bond, Andrew D.
Sutherland, John D.
author_facet Liu, Ziwei
Wu, Long-Fei
Bond, Andrew D.
Sutherland, John D.
author_sort Liu, Ziwei
collection PubMed
description Prebiotically plausible ferrocyanide–ferricyanide photoredox cycling oxidatively converts thiourea to cyanamide, whilst HCN is reductively homologated to intermediates which either react directly with the cyanamide giving 2-aminoazoles, or have the potential to do so upon loss of HCN from the system. Thiourea itself is produced by heating ammonium thiocyanate, a product of the reaction of HCN and hydrogen sulfide under UV irradiation.
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spelling pubmed-78083122021-01-22 Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis Liu, Ziwei Wu, Long-Fei Bond, Andrew D. Sutherland, John D. Chem Commun (Camb) Chemistry Prebiotically plausible ferrocyanide–ferricyanide photoredox cycling oxidatively converts thiourea to cyanamide, whilst HCN is reductively homologated to intermediates which either react directly with the cyanamide giving 2-aminoazoles, or have the potential to do so upon loss of HCN from the system. Thiourea itself is produced by heating ammonium thiocyanate, a product of the reaction of HCN and hydrogen sulfide under UV irradiation. Royal Society of Chemistry 2020-11-14 2020-10-08 /pmc/articles/PMC7808312/ /pubmed/33151212 http://dx.doi.org/10.1039/d0cc05752e Text en This journal is © The Royal Society of Chemistry 2020 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Liu, Ziwei
Wu, Long-Fei
Bond, Andrew D.
Sutherland, John D.
Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title_full Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title_fullStr Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title_full_unstemmed Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title_short Photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
title_sort photoredox chemistry in the synthesis of 2-aminoazoles implicated in prebiotic nucleic acid synthesis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7808312/
https://www.ncbi.nlm.nih.gov/pubmed/33151212
http://dx.doi.org/10.1039/d0cc05752e
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AT bondandrewd photoredoxchemistryinthesynthesisof2aminoazolesimplicatedinprebioticnucleicacidsynthesis
AT sutherlandjohnd photoredoxchemistryinthesynthesisof2aminoazolesimplicatedinprebioticnucleicacidsynthesis

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