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Syntheses And Reactions Of α-benzotriazolylenamines: Stable Analogs Of α-chlorenamines

A. Katritzky, Daniel A. Nicols, M. Voronkov
Published 2000 · Chemistry

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Synthetic routes to and utility of α-benzotriazolylenamines have been explored. α- Benzotriazolylenamines 3a-g, 4a-f and 5a,b were successfully synthesized (i) from N-(trans- buten-1-yl)-N-methylaniline (2) by reaction with 1-chloro-1H-1,2,3-benzotriazole, followed by base induced elimination of HCl and (ii) from amides 1a-g using benzotriazole, POCl3 and NEt3 in CH3CN. The utility of 3a-g, 4a-f and 5a,b as stable alternatives to α-haloenamines was demonstrated by the successful reaction of N-(1-(2H-1,2,3-benzotriazol-2-yl)-2-methylprop-1- enyl)-N-methylaniline (5a) with phenylethynylzinc chloride to form N-methyl-N-(2-methyl-1-(2- phenylethynyl)-1-propenyl)aniline (7).
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