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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2018
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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. |
format | Online Article Text |
id | pubmed-6641926 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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