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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...

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Autores principales: Soda, Anil Kumar, Chinthapally, Krishna Prasad, C. S., Phani Krishna, Chilaka, Sai Krishna, Madabhushi, Sridhar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
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.
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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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