Generation of N–H Imines from α-Azidocarboxylic Acids through Ru-Catalyzed Decarboxylation

Autor:	Hwi Yul Jo, Ewa Pietrasiak, Young Ho Rhee, Jeong Min Lee, Jaiwook Park, Eunsung Lee
Rok vydání:	2021
Předmět:	Molecular Structure Decarboxylation Organic Chemistry Visible light irradiation Condensation Medicinal chemistry Catalysis chemistry.chemical_compound Aniline Benzylamine chemistry Imines Oxidation-Reduction Bond cleavage
Zdroj:	The Journal of Organic Chemistry. 86:17409-17417
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01841
Popis:	A new method for the synthesis of N-H imines from α-azidocarboxylic acids was developed, which proceeds through decarboxylative C-C bond cleavage catalyzed by a commercial diruthenium complex ([CpRu(CO)2]2) under visible light irradiation at room temperature within several minutes. The reactive products undergo condensation, which forms cyclic trimers (2,4,6-trialkylhexahydro-1,3,5-triazines) or linear N,N'-bis(arylmethylidene)arylmethanediamines in quantitative yields. Alternatively, the N-H imines can be trapped with benzylamine and 2-(aminomethyl)aniline, providing stable N-benylimines and tetrahydroquinazolines, respectively. Subsequent oxidation of tetrahydroquinazolines produced quinazolines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::d2e5cf2f3f9ea5b6a0e1ab712995a964 https://doi.org/10.1021/acs.joc.1c01841 Zobrazit plný text záznamu