Silver-catalyzed nitration/annulation of 2-alkynylanilines for a tunable synthesis of nitrated indoles and indazole-2-oxides

Autor:	Pei-Jun Cai, Shu-Jiang Tu, Rong Wang, Tian-Shu Zhang, Wen-Juan Hao, Bo Jiang
Rok vydání:	2019
Předmět:	chemistry.chemical_compound Indazole Annulation chemistry 010405 organic chemistry Nitration Organic Chemistry Organic chemistry Nitrite 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis
Zdroj:	Organic Chemistry Frontiers. 6:2968-2973
ISSN:	2052-4129
DOI:	10.1039/c9qo00715f
Popis:	Two new types of silver-catalyzed nitration–annulations of 2-alkynylanilines with tert-butyl nitrite (TBN) were reported, leading to the selective formation of a variety of nitrated indoles and indazole-2-oxides by changing the N-protection of 2-alkynylanilines. Ag-Catalyzed nitration–annulation of N-sulfonyl 2-alkynylanilines without C4 substituents afforded 5-nitroindoles under neutral-redox conditions, whereas the presence of C5 substituents gave 7-nitroindoles through silver catalysis. N-Methyl 2-alkynylanilines underwent a completely different process to furnish aroyl indazole-2-oxides.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2510fb710b0d6f6668422d13f474a2ac https://doi.org/10.1039/c9qo00715f Zobrazit plný text záznamu