S 98 Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine / A. Yu. Vigorov, I. A. Nizova, K. E. Shalunova, A. N. Grishakov, L. Sh. Sadretdinova, I. N. Ganebnuikh, M. A. Ezhikova, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 873-881 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 4-AMINOPROLINE -- 4-AMINOPROLINE -- INDOLE Аннотация: Nucleophilic substitution of the halogen atom in dimethyl (S)-4-bromoglutamate followed by removal of the protecting groups and closure of a lactam ring afforded (2S,4S)-4-(indolin-1-yl)-5-oxoproline. The indoline fragment was oxidized into the indole fragment to give (2S,4S)-4-(indol-1-yl)-5-oxoproline; reduction of the carbonyl groups with BH3 yielded (2S,4S)-4-(indol-1-yl)prolines and (2S,4S)-2-hydroxymethyl-4-(indol-1-yl)pyrrolidines. Reduction of (2S,4S)-4-arylamino-5-oxoprolines with BH3 to the corresponding (2S,4S)-4-arylaminoprolines and (2S,4S)-4-arylamino-2-hydroxymethylpyrrolidines was studied \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 873-881.pdf |