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1,2-Didehydrophenothiazines: Preparation of 1-Alkyl and 1-Aryl-substituted Phenothiazines by Lithium-directed Alkylation
A general route to 1-alkyl substituted phenothiazines is described.Reactions of 2-chlorophenothiazine with an excess of methyl-, n-butyl-, s-butyl-, t-butyl- or phenyl-lithiums give the corresponding 1-substituted phenothiazines via 10-lithio-1,2-dehydrophenothiazine.Attempts to trap the presumed 1,10-dilithio intermediate failed.The reaction of 1-chlorophenothiazine with s-butyl-lithium results in preferential metallation of the 9-position. 2-Chlorophenothiazine reacts with nitrogen nucleophiles (lithium dialkylamides) to give 2-substituted products.
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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem