A base-mediated synthesis of < em > N < /em > -hydroxy- and < em > N < /em > -alkoxyindoles from 2-nitrostyrenes

Tetrahedron. 2023 Sep 7;144:133578. doi: 10.1016/j.tet.2023.133578. Epub 2023 Aug 6.ABSTRACTSequential treatment of alkyl 2-(2-nitroaryl)-2-butenoates with potassium tert-butoxide and an electrophile, such as methyl iodide, benzyl bromide and allyl bromide, afforded N-alkoxyindoles. In related reactions, using sodium tert-pentoxide as the base with or without in situ addition of an electrophile afforded N-alkoxy- and N-hydroxyindoles, respectively. Electrophiles such as dimethylsulfate, p-tosyl chloride, and acetic anhydride afforded moderate yields of the respective N-methoxy-, N-tosyloxy, and N-acetoxyindoles, while methyl iodide, benzyl bromide, and 1-bromohexane failed to form alkylated products using sodium tert-pentoxide as the base.PMID:37680993 | PMC:PMC10482417 | DOI:10.1016/j.tet.2023.133578

Source: Tetrahedron - September 8, 2023 Category: Chemistry Authors: Blaine T McClay Katharine E Lambson Serge R Banini Tural N Akhmedov Bj örn C G Söderberg Source Type: research