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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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Detalles Bibliográficos
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
Descripción
Sumario: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.