Base-Mediated Intramolecular Cyclization of α-Nitroethylallenic Esters as a Synthetic Route to 5-Hydroxy-3-pyrrolin-2-ones

Autor:	Kishor Mohanan, Sandeep Kumar, Mohd Khalid Zaheer, Narendra Kumar Vaishanv, Ruchir Kant
Rok vydání:	2021
Předmět:	Lactams Cyclization 010405 organic chemistry Chemistry Organic Chemistry Intramolecular cyclization Esters 010402 general chemistry Base (exponentiation) 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences
Zdroj:	The Journal of Organic Chemistry. 86:5630-5638
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c00109
Popis:	An unprecedented Cs2CO3-mediated intramolecular cyclization/rearrangement cascade that transforms α-nitroethylallenic esters to functionalized pyrrolin-2-ones has been uncovered. This reaction provides a new and practical approach for the synthesis of medicinally privileged 5-hydroxy-3-pyrrolin-2-ones under mild conditions. The broad potential of this new method was demonstrated by an efficient Au/Ag-catalyzed heteroarylation of 5-hydroxy-3-pyrrolin-2-ones employing electron-rich heteroarenes to furnish heteroaryl-lactam derivatives.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8cb068159e7b1c73ad7ba6907d8264cc https://doi.org/10.1021/acs.joc.1c00109 Zobrazit plný text záznamu