Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins

Cu-catalyzed A(3) coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with...

Descripción completa

Detalles Bibliográficos
Autores principales: Reddy, Maddi Sridhar, Thirupathi, Nuligonda, Haribabu, Madala
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566765/
https://www.ncbi.nlm.nih.gov/pubmed/23400373
http://dx.doi.org/10.3762/bjoc.9.21
_version_ 1782258599867711488
author Reddy, Maddi Sridhar
Thirupathi, Nuligonda
Haribabu, Madala
author_facet Reddy, Maddi Sridhar
Thirupathi, Nuligonda
Haribabu, Madala
author_sort Reddy, Maddi Sridhar
collection PubMed
description Cu-catalyzed A(3) coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields.
format Online
Article
Text
id pubmed-3566765
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-35667652013-02-11 Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins Reddy, Maddi Sridhar Thirupathi, Nuligonda Haribabu, Madala Beilstein J Org Chem Full Research Paper Cu-catalyzed A(3) coupling of ethoxyacetylene, pyrrolidine and salicylaldehydes led to a concomitant cycloisomerization followed by hydrolysis of the resultant vinyl ether to afford coumarins in a cascade process. The reaction proceeded through exclusive 6-endo-dig cyclization and is compatible with halo and keto groups giving coumarins in good to moderate yields. Beilstein-Institut 2013-01-28 /pmc/articles/PMC3566765/ /pubmed/23400373 http://dx.doi.org/10.3762/bjoc.9.21 Text en Copyright © 2013, Reddy et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Reddy, Maddi Sridhar
Thirupathi, Nuligonda
Haribabu, Madala
Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title_full Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title_fullStr Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title_full_unstemmed Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title_short Tandem aldehyde–alkyne–amine coupling/cycloisomerization: A new synthesis of coumarins
title_sort tandem aldehyde–alkyne–amine coupling/cycloisomerization: a new synthesis of coumarins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566765/
https://www.ncbi.nlm.nih.gov/pubmed/23400373
http://dx.doi.org/10.3762/bjoc.9.21
work_keys_str_mv AT reddymaddisridhar tandemaldehydealkyneaminecouplingcycloisomerizationanewsynthesisofcoumarins
AT thirupathinuligonda tandemaldehydealkyneaminecouplingcycloisomerizationanewsynthesisofcoumarins
AT haribabumadala tandemaldehydealkyneaminecouplingcycloisomerizationanewsynthesisofcoumarins

Ejemplares similares