3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization

[Image: see text] A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o-hydroxyphenyl propargyl alcohols (o-HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o-quinone methides...

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Autores principales: Rajesh, Manda, Singam, Maneesh Kumar Reddy, Gadi, Ranjith Kumar, Sridhar Reddy, Maddi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644147/
https://www.ncbi.nlm.nih.gov/pubmed/31458335
http://dx.doi.org/10.1021/acsomega.8b02480
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author Rajesh, Manda
Singam, Maneesh Kumar Reddy
Gadi, Ranjith Kumar
Sridhar Reddy, Maddi
author_facet Rajesh, Manda
Singam, Maneesh Kumar Reddy
Gadi, Ranjith Kumar
Sridhar Reddy, Maddi
author_sort Rajesh, Manda
collection PubMed
description [Image: see text] A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o-hydroxyphenyl propargyl alcohols (o-HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o-quinone methides (o-QMs) were the putative reaction intermediates ensued from dehydration of o-HPPA. Our study revealed that the o-QM was so choosy in selection of the nucleophiles for the key Michael addition reaction.
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spelling pubmed-66441472019-08-27 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization Rajesh, Manda Singam, Maneesh Kumar Reddy Gadi, Ranjith Kumar Sridhar Reddy, Maddi ACS Omega [Image: see text] A facile route to 3-sulfonylated and 3-(1-benzotriazolyl)-benzofurans is achieved from readily available o-hydroxyphenyl propargyl alcohols (o-HPPAs) and bench-top sodium sulfonylates and benzotriazoles with no assistance of any reagent or catalyst. Bifunctional o-quinone methides (o-QMs) were the putative reaction intermediates ensued from dehydration of o-HPPA. Our study revealed that the o-QM was so choosy in selection of the nucleophiles for the key Michael addition reaction. American Chemical Society 2018-12-12 /pmc/articles/PMC6644147/ /pubmed/31458335 http://dx.doi.org/10.1021/acsomega.8b02480 Text en Copyright © 2018 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 Rajesh, Manda
Singam, Maneesh Kumar Reddy
Gadi, Ranjith Kumar
Sridhar Reddy, Maddi
3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title_full 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title_fullStr 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title_full_unstemmed 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title_short 3-Heterosubstituted Benzofurans from Hydroxyphenyl Propargyl Alcohols via ortho-Quinone Methide through a Metal-/Catalyst-Free Conjugate Addition/Oxy-Cyclization
title_sort 3-heterosubstituted benzofurans from hydroxyphenyl propargyl alcohols via ortho-quinone methide through a metal-/catalyst-free conjugate addition/oxy-cyclization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644147/
https://www.ncbi.nlm.nih.gov/pubmed/31458335
http://dx.doi.org/10.1021/acsomega.8b02480
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