Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones

[Image: see text] A general method for highly functionalized 2-pyrones via a base-mediated sequential vinylogous addition and cyclization of γ-phosphonyl/sulfonyl crotonates and ynones are described. An exclusive E-geometry with respect to the newly generated olefin substituent at C3 of pyrone was o...

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Autores principales: Parameshwar, Matam, Rajesh, Manda, Balasubramanian, Sridhar, Sridhar Reddy, Maddi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6854826/
https://www.ncbi.nlm.nih.gov/pubmed/31737846
http://dx.doi.org/10.1021/acsomega.9b02874
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author Parameshwar, Matam
Rajesh, Manda
Balasubramanian, Sridhar
Sridhar Reddy, Maddi
author_facet Parameshwar, Matam
Rajesh, Manda
Balasubramanian, Sridhar
Sridhar Reddy, Maddi
author_sort Parameshwar, Matam
collection PubMed
description [Image: see text] A general method for highly functionalized 2-pyrones via a base-mediated sequential vinylogous addition and cyclization of γ-phosphonyl/sulfonyl crotonates and ynones are described. An exclusive E-geometry with respect to the newly generated olefin substituent at C3 of pyrone was observed. Imino glyoxalates and glycine imines similarly reacted with ynones to deliver 3-imino pyrones.
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spelling pubmed-68548262019-11-15 Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones Parameshwar, Matam Rajesh, Manda Balasubramanian, Sridhar Sridhar Reddy, Maddi ACS Omega [Image: see text] A general method for highly functionalized 2-pyrones via a base-mediated sequential vinylogous addition and cyclization of γ-phosphonyl/sulfonyl crotonates and ynones are described. An exclusive E-geometry with respect to the newly generated olefin substituent at C3 of pyrone was observed. Imino glyoxalates and glycine imines similarly reacted with ynones to deliver 3-imino pyrones. American Chemical Society 2019-10-30 /pmc/articles/PMC6854826/ /pubmed/31737846 http://dx.doi.org/10.1021/acsomega.9b02874 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Parameshwar, Matam
Rajesh, Manda
Balasubramanian, Sridhar
Sridhar Reddy, Maddi
Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title_full Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title_fullStr Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title_full_unstemmed Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title_short Base Mediated Tandem Vinylogous Addition and Cyclization of γ-Phosphonyl/Sulfonyl Crotonates and Ynones: Synthesis of Functionalized 2-Pyrones
title_sort base mediated tandem vinylogous addition and cyclization of γ-phosphonyl/sulfonyl crotonates and ynones: synthesis of functionalized 2-pyrones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6854826/
https://www.ncbi.nlm.nih.gov/pubmed/31737846
http://dx.doi.org/10.1021/acsomega.9b02874
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