TY - JOUR
T1 - Synthesis of tetrahydro-β-carbolines via radical cyclization of 2-alkenylthioanilides
AU - Iwadate, Manami
AU - Yamashita, Tohru
AU - Tokuyama, Hidetoshi
AU - Fukuyama, Tohru
PY - 2005/12/31
Y1 - 2005/12/31
N2 - A synthetic protocol of 1,2,3,4-tetrahydro-β-carbolines from o-alkenylaniline and α-amino acid was developed. Condensation of α-amino acids with 2-alkenylaniline derived from quinoline gave o-alkenylanilides. Conversion of the anilides to thioanilides was effected with Lawesson's reagent in the presence of pyridine, which was crucial to suppress epimerization of the chiral center. After formation of an indole skeleton by radical cyclization, 1,2,3,4-tetrahydro-β-carbolines were obtained via intramolecular N-alkylation.
AB - A synthetic protocol of 1,2,3,4-tetrahydro-β-carbolines from o-alkenylaniline and α-amino acid was developed. Condensation of α-amino acids with 2-alkenylaniline derived from quinoline gave o-alkenylanilides. Conversion of the anilides to thioanilides was effected with Lawesson's reagent in the presence of pyridine, which was crucial to suppress epimerization of the chiral center. After formation of an indole skeleton by radical cyclization, 1,2,3,4-tetrahydro-β-carbolines were obtained via intramolecular N-alkylation.
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U2 - 10.3987/COM-05-S(K)11
DO - 10.3987/COM-05-S(K)11
M3 - Article
AN - SCOPUS:33646896738
SN - 0385-5414
VL - 66
SP - 241
EP - 249
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -