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NaNO 2 /K 2 S 2 O 8 ‐mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3‐Nitro‐ and 3‐Nitrosoindoles
Author(s) -
Shoberu Adedamola,
Li ChengKun,
Tao ZeKun,
Zhang GuoYu,
Zou JianPing
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900070
Subject(s) - chemistry , nitration , nitrosation , nitroso , pyrrole , oxime , nitro , indole test , medicinal chemistry , nitroso compounds , nano , combinatorial chemistry , organic chemistry , alkyl , physics , quantum mechanics
A mild and selective radical nitration/nitrosation of indoles with NaNO 2 using K 2 S 2 O 8 as oxidant is developed. Free (NH)‐indoles and N‐methyl indoles furnished 3‐nitro‐ and 3‐nitrosoindoles respectively, in good yields. Contrary to existing protocols, pyrrole selectively afforded 3‐nitropyrrole. Mechanistic studies showed that the reaction proceeded via an initial formation of nitroso/oxime intermediate, which is further oxidized to the corresponding 3‐nitroindole depending on the substitution on the indole N‐atom. Furthermore, synthetic transformations were carried out on the synthesized products towards accessing other valuable compounds.