Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate

Two independent methods generating 7-azaindoxyl as an intermediate verify that 7,7′-diazaindirubin is formed exclusively over 7,7′-diazaindigo. This contrasts with long-standing knowledge related to the reactivity of indoxyl, which proceeds via a radical-initiated homodimerization process, leading t...

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Autores principales: Shriver, James A., Wang, Katelyn R., Patterson, Andrew C., DeYoung, James R., Lipsius, Richard J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057083/
https://www.ncbi.nlm.nih.gov/pubmed/35517962
http://dx.doi.org/10.1039/d0ra07144g
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author Shriver, James A.
Wang, Katelyn R.
Patterson, Andrew C.
DeYoung, James R.
Lipsius, Richard J.
author_facet Shriver, James A.
Wang, Katelyn R.
Patterson, Andrew C.
DeYoung, James R.
Lipsius, Richard J.
author_sort Shriver, James A.
collection PubMed
description Two independent methods generating 7-azaindoxyl as an intermediate verify that 7,7′-diazaindirubin is formed exclusively over 7,7′-diazaindigo. This contrasts with long-standing knowledge related to the reactivity of indoxyl, which proceeds via a radical-initiated homodimerization process, leading to indigo. A series of experiments confirms 7-azaindoxyl as an intermediate with results suggesting a condensation pathway followed by oxidation.
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spelling pubmed-90570832022-05-04 Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate Shriver, James A. Wang, Katelyn R. Patterson, Andrew C. DeYoung, James R. Lipsius, Richard J. RSC Adv Chemistry Two independent methods generating 7-azaindoxyl as an intermediate verify that 7,7′-diazaindirubin is formed exclusively over 7,7′-diazaindigo. This contrasts with long-standing knowledge related to the reactivity of indoxyl, which proceeds via a radical-initiated homodimerization process, leading to indigo. A series of experiments confirms 7-azaindoxyl as an intermediate with results suggesting a condensation pathway followed by oxidation. The Royal Society of Chemistry 2020-10-06 /pmc/articles/PMC9057083/ /pubmed/35517962 http://dx.doi.org/10.1039/d0ra07144g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Shriver, James A.
Wang, Katelyn R.
Patterson, Andrew C.
DeYoung, James R.
Lipsius, Richard J.
Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title_full Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title_fullStr Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title_full_unstemmed Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title_short Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
title_sort exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057083/
https://www.ncbi.nlm.nih.gov/pubmed/35517962
http://dx.doi.org/10.1039/d0ra07144g
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