Copper-catalyzed cascade reaction: synthesis of pyrimido[4,5-b]quinolinones from 2-chloroquinoline-3-carbonitriles with (aryl)methanamines

Autor:	Tanu Gupta, Radhey M. Singh, Jay Bahadur Singh, Kalpana Mishra
Rok vydání:	2018
Předmět:	Nucleophilic addition Nitrile 010405 organic chemistry Chemistry Aryl Iminium General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Cascade reaction Sodium hydroxide Amide Reagent Materials Chemistry
Zdroj:	New Journal of Chemistry. 42:3310-3314
ISSN:	1369-9261 1144-0546
DOI:	10.1039/c7nj04689h
Popis:	Cu-catalyzed cascade reaction of 2-chloroquinoline-3-carbonitriles with benzyl amines and sodium hydroxide in aerobic atmosphere has been developed for the synthesis of pyrimido[4,5-b]quinoline-4-ones. The reaction proceeds sequentially via Ullmann-coupling and conversion of nitrile to amide followed by nucleophilic addition of amide nitrogen onto iminium carbon and air oxidation. Reagents and substrates are cheap and easily available/accessible. Plausible mechanism of reaction is also discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::69adc10620e444db536c8b0741858246 https://doi.org/10.1039/c7nj04689h Zobrazit plný text záznamu