Regiodivergent Synthesis of 4,5′- and 4,4′-Imidazolinyl Spiropyrazolones from 4-Alkylidene Pyrazolones and Amidines

Autor:	Ran Hong, Hui Xu, Ze Zhang, Ming-Yue Weng, Guan-Wu Wang, Rong-Lu Huang
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Chemistry Organic Chemistry Regioselectivity Pyrazolones Physical and Theoretical Chemistry Biochemistry Toluene Combinatorial chemistry
Zdroj:	Organic Letters. 23:5305-5310
ISSN:	1523-7052 1523-7060
Popis:	The solvent-free reaction of 4-alkylidene pyrazolones with amidines can furnish 4,5'-imidazolinyl spiropyrazolones in good to excellent yields when promoted by N-iodosuccinimide under solvent-free ball-milling conditions, whereas it almost exclusively affords 4,4'-imidazolinyl spiropyrazolones if mediated by N-bromosuccinimide in heated toluene. On the basis of this switchable cyclization strategy, a powerful metal-free method for regioselective and diastereoselective synthesis of structurally diverse 4,5'- and 4,4'-imidazolinyl spiropyrazolones has been successfully developed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a768b42ce73deccdc28b13ce90d80586 https://doi.org/10.1021/acs.orglett.1c01475 Zobrazit plný text záznamu