TY - JOUR
T1 - 2-(2-aminophenyl)-acetaldehyde dimethyl acetal
T2 - A novel reagent for the protection of carboxylic acids
AU - Arai, Eri
AU - Tokuyama, Hidetoshi
AU - Linsell, Martin S.
AU - Fukuyama, Tohru
PY - 1998/1/1
Y1 - 1998/1/1
N2 - 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.
AB - 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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U2 - 10.1016/S0040-4039(97)10491-9
DO - 10.1016/S0040-4039(97)10491-9
M3 - Article
AN - SCOPUS:0031962821
SN - 0040-4039
VL - 39
SP - 71
EP - 74
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 1-2
ER -