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Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids
The one-pot domino reaction of ethyl (Z)-3-amino-3-phenylacrylates with 2-amino-N-alkyl/arylbenzamides under Lewis acid catalysis was described as an effective way to construct novel spiro [pyrrole-3,2′-quinazoline] carboxylate derivatives. By combining substituted alkyl/aryl amides with spiro annul...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10187044/ https://www.ncbi.nlm.nih.gov/pubmed/37200694 http://dx.doi.org/10.1039/d3ra02639f |
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author | Soda, Anil Kumar Chinthapally, Krishna Prasad C. S., Phani Krishna Chilaka, Sai Krishna Madabhushi, Sridhar |
author_facet | Soda, Anil Kumar Chinthapally, Krishna Prasad C. S., Phani Krishna Chilaka, Sai Krishna Madabhushi, Sridhar |
author_sort | Soda, Anil Kumar |
collection | PubMed |
description | The one-pot domino reaction of ethyl (Z)-3-amino-3-phenylacrylates with 2-amino-N-alkyl/arylbenzamides under Lewis acid catalysis was described as an effective way to construct novel spiro [pyrrole-3,2′-quinazoline] carboxylate derivatives. By combining substituted alkyl/aryl amides with spiro annulated 1H-pyrrole-2,3-diones, this method provides a novel way for producing spiro pyrrole derivatives in good to excellent yields. The current procedure has a number of benefits, including quicker reaction times, a broad tolerance range for functional groups, and the ability to synthesize 2,3-dihydroquinazolin-4(1H)-ones that are of biological importance and take part in organic transformations. This is the first use of molecular hybridization involving linking with pyrrole derivatives and dihydroquinazolin-4(1H)-ones. |
format | Online Article Text |
id | pubmed-10187044 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-101870442023-05-17 Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids Soda, Anil Kumar Chinthapally, Krishna Prasad C. S., Phani Krishna Chilaka, Sai Krishna Madabhushi, Sridhar RSC Adv Chemistry The one-pot domino reaction of ethyl (Z)-3-amino-3-phenylacrylates with 2-amino-N-alkyl/arylbenzamides under Lewis acid catalysis was described as an effective way to construct novel spiro [pyrrole-3,2′-quinazoline] carboxylate derivatives. By combining substituted alkyl/aryl amides with spiro annulated 1H-pyrrole-2,3-diones, this method provides a novel way for producing spiro pyrrole derivatives in good to excellent yields. The current procedure has a number of benefits, including quicker reaction times, a broad tolerance range for functional groups, and the ability to synthesize 2,3-dihydroquinazolin-4(1H)-ones that are of biological importance and take part in organic transformations. This is the first use of molecular hybridization involving linking with pyrrole derivatives and dihydroquinazolin-4(1H)-ones. The Royal Society of Chemistry 2023-05-16 /pmc/articles/PMC10187044/ /pubmed/37200694 http://dx.doi.org/10.1039/d3ra02639f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/ |
spellingShingle | Chemistry Soda, Anil Kumar Chinthapally, Krishna Prasad C. S., Phani Krishna Chilaka, Sai Krishna Madabhushi, Sridhar Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title | Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title_full | Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title_fullStr | Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title_full_unstemmed | Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title_short | Lewis acid catalyzed spiro annulation of (Z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
title_sort | lewis acid catalyzed spiro annulation of (z)-3-amino-acrylates with 2-amino arylbenzamides: one-pot synthesis of pyrrole–quinazoline hybrids |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10187044/ https://www.ncbi.nlm.nih.gov/pubmed/37200694 http://dx.doi.org/10.1039/d3ra02639f |
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