Tetrahedron Letters p. 71 - 74 (1998)
Update date:2022-08-03
Topics:
Arai, Eri
Tokuyama, Hidetoshi
Linsell, Martin S.
Fukuyama, Tohru
The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes.
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