Access to Indole-Annulated Medium-Sized Lactams through Protonation/Deuteration-Induced Ring-Opening of Spiroindolines

Autor:	Jianhui Qiao, Huili Liu, Shaozhong Wang
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	Indole test General Chemical Engineering Diastereomer Protonation General Chemistry Ring (chemistry) Medicinal chemistry Article chemistry.chemical_compound Chemistry chemistry Nucleophile Lactam Deuterated methanol Brønsted–Lowry acid–base theory QD1-999
Zdroj:	ACS Omega ACS Omega, Vol 6, Iss 38, Pp 25049-25061 (2021)
ISSN:	2470-1343
Popis:	A protocol has been developed to access indole-annulated eight- and nine-membered lactams through protonation-induced ring-opening of spiroindolines, which are dearomative Heck products of tetrahydro-β-carbolines or hexahydroazepino[3,4-b]indoles. Bronsted acids and nucleophiles were explored and compared in the transformation. A combination of deuterated hydrochloride and deuterated methanol enables deuterative ring-opening of spiroindolines to afford medium-sized lactam diastereoisomers with a deuterium content ratio around 1:1.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2e3d067b98351785ab07a630bfc2c049 http://europepmc.org/articles/PMC8482774 Zobrazit plný text záznamu