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One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides

[Image: see text] A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal–Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to...

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Autores principales: Mupparapu, Nagaraju, Khan, Shahnawaz, Bandhoria, Pankaj, Athimoolam, Shunmuganarayanan, Ahmed, Qazi Naveed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641926/
https://www.ncbi.nlm.nih.gov/pubmed/31458749
http://dx.doi.org/10.1021/acsomega.8b00715
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author Mupparapu, Nagaraju
Khan, Shahnawaz
Bandhoria, Pankaj
Athimoolam, Shunmuganarayanan
Ahmed, Qazi Naveed
author_facet Mupparapu, Nagaraju
Khan, Shahnawaz
Bandhoria, Pankaj
Athimoolam, Shunmuganarayanan
Ahmed, Qazi Naveed
author_sort Mupparapu, Nagaraju
collection PubMed
description [Image: see text] A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal–Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O–H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated (Z)-2-furanyl-acrylamides.
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spelling pubmed-66419262019-08-27 One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides Mupparapu, Nagaraju Khan, Shahnawaz Bandhoria, Pankaj Athimoolam, Shunmuganarayanan Ahmed, Qazi Naveed ACS Omega [Image: see text] A novel one-pot tandem process involving Knoevenagel condensation, Michael addition, selective amidation, and Paal–Knorr cyclization to diverse functionalized 3-hydroxy-2-furanyl-acrylamides from simple 2-oxoaldehydes and aroylacetonitriles was presented. Attempts were also made to expand the scope of the reaction to different 2-heteroarylfurans. The packing diagram of the molecules viewed down along the α-axis of the unit cell showed a characteristic intramolecular classical O–H···O hydrogen bond between hydroxyl and carbonyl O atoms leading to self-associated (Z)-2-furanyl-acrylamides. American Chemical Society 2018-05-21 /pmc/articles/PMC6641926/ /pubmed/31458749 http://dx.doi.org/10.1021/acsomega.8b00715 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 Mupparapu, Nagaraju
Khan, Shahnawaz
Bandhoria, Pankaj
Athimoolam, Shunmuganarayanan
Ahmed, Qazi Naveed
One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title_full One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title_fullStr One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title_full_unstemmed One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title_short One-Pot Tandem Approach to Functionalized 3-Hydroxy-2-furanyl-acrylamides
title_sort one-pot tandem approach to functionalized 3-hydroxy-2-furanyl-acrylamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641926/
https://www.ncbi.nlm.nih.gov/pubmed/31458749
http://dx.doi.org/10.1021/acsomega.8b00715
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