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Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases

[Image: see text] Woollins’ reagent, [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide], serving as a selenating-reductive cycloaddition reagent, reacts with nonconjugated amido-Schiff bases to give the corresponding six-membered 1,3,4-selenadiazoles via a ring-expansion accompanied by an ad...

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Autores principales: Hua, Guoxiong, Cordes, David B., Slawin, Alexandra M. Z., Woollins, J. Derek
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7254804/
https://www.ncbi.nlm.nih.gov/pubmed/32478265
http://dx.doi.org/10.1021/acsomega.0c01064
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author Hua, Guoxiong
Cordes, David B.
Slawin, Alexandra M. Z.
Woollins, J. Derek
author_facet Hua, Guoxiong
Cordes, David B.
Slawin, Alexandra M. Z.
Woollins, J. Derek
author_sort Hua, Guoxiong
collection PubMed
description [Image: see text] Woollins’ reagent, [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide], serving as a selenating-reductive cycloaddition reagent, reacts with nonconjugated amido-Schiff bases to give the corresponding six-membered 1,3,4-selenadiazoles via a ring-expansion accompanied by an additional selenation/cyclization to the imine bond and C=O group; meanwhile, under the same reaction conditions, the selenation of conjugated amido-Schiff bases leads to a series of fused heterocycles with two five-membered rings. Eight single-crystal X-ray structures confirming the formation of these five- and six-membered heterocycles are discussed.
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spelling pubmed-72548042020-05-29 Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases Hua, Guoxiong Cordes, David B. Slawin, Alexandra M. Z. Woollins, J. Derek ACS Omega [Image: see text] Woollins’ reagent, [2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide], serving as a selenating-reductive cycloaddition reagent, reacts with nonconjugated amido-Schiff bases to give the corresponding six-membered 1,3,4-selenadiazoles via a ring-expansion accompanied by an additional selenation/cyclization to the imine bond and C=O group; meanwhile, under the same reaction conditions, the selenation of conjugated amido-Schiff bases leads to a series of fused heterocycles with two five-membered rings. Eight single-crystal X-ray structures confirming the formation of these five- and six-membered heterocycles are discussed. American Chemical Society 2020-05-12 /pmc/articles/PMC7254804/ /pubmed/32478265 http://dx.doi.org/10.1021/acsomega.0c01064 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Hua, Guoxiong
Cordes, David B.
Slawin, Alexandra M. Z.
Woollins, J. Derek
Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title_full Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title_fullStr Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title_full_unstemmed Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title_short Novel Five- and Six-Membered Rings of Phosphorus–Selenium Heterocycles from Selenation of Amido-Schiff Bases
title_sort novel five- and six-membered rings of phosphorus–selenium heterocycles from selenation of amido-schiff bases
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7254804/
https://www.ncbi.nlm.nih.gov/pubmed/32478265
http://dx.doi.org/10.1021/acsomega.0c01064
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