N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines

[Image: see text] An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes...

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Autores principales: Evans, Lindsay E., Cheeseman, Matthew D., Jones, Keith
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2012
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3390909/
https://www.ncbi.nlm.nih.gov/pubmed/22734502
http://dx.doi.org/10.1021/ol301561a
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author Evans, Lindsay E.
Cheeseman, Matthew D.
Jones, Keith
author_facet Evans, Lindsay E.
Cheeseman, Matthew D.
Jones, Keith
author_sort Evans, Lindsay E.
collection PubMed
description [Image: see text] An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes a cyclization reaction upon an oxime derived from hydroxylamine-O-sulfonic acid to form the N–N bond of the product.
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spelling pubmed-33909092012-07-06 N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines Evans, Lindsay E. Cheeseman, Matthew D. Jones, Keith Org Lett [Image: see text] An efficient one-pot synthesis of N-aryl[3,4-d]pyrazolopyrimidines in good yield and under mild reaction conditions is described. By exploiting electron-deficient hydroxylamines, the substituted oxime products were formed with very high E-diastereoselectivity. The key step utilizes a cyclization reaction upon an oxime derived from hydroxylamine-O-sulfonic acid to form the N–N bond of the product. American Chemical Society 2012-06-26 2012-07-06 /pmc/articles/PMC3390909/ /pubmed/22734502 http://dx.doi.org/10.1021/ol301561a Text en Copyright © 2012 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Evans, Lindsay E.
Cheeseman, Matthew D.
Jones, Keith
N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title_full N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title_fullStr N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title_full_unstemmed N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title_short N–N Bond-Forming Cyclization for the One-Pot Synthesis of N-Aryl[3,4-d]pyrazolopyrimidines
title_sort n–n bond-forming cyclization for the one-pot synthesis of n-aryl[3,4-d]pyrazolopyrimidines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3390909/
https://www.ncbi.nlm.nih.gov/pubmed/22734502
http://dx.doi.org/10.1021/ol301561a
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