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 |
1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines / V. S. Moshkin, V. Ya. Sosnovskikh, P. A. Slepukhin, Gerd-Volker Röschenthalerc // Mendeleev Communications. - 2012. - Vol.22, №1. - С. 29-31 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): COUMARINS -- AZOMETHINE YLIDES -- PYRROLIDINES Аннотация: Reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes proceeds regio- and stereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines as a result of 1,3-dipolar cycloaddition of the intermediate azomethine ylides at the Δ3-bond of the coumarins \\\\Expert2\\nbo\\Mendeleev Communications\\2012, v.22, p. 29.pdf |
H 65 Highly diastereoselective 1,3-dipolar cycloaddition of nonstabilized azomethine ylides to 3-nitro-2-trihalomethyl-2H-chromenes: synthesis of 1-benzopyrano[3,4-c]pyrrolidines [Electronic resource] / V. Yu. Korotaev, A. Yu. Barkov, V. S. Moshkin, E. G. Matochkina, M. I. Kodess, V. Ya. Sosnovskikh // Tetrahedron. - 2013. - Vol.69, №40. - P8602-8608. - Bibliogr. : p. 8608 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3-NITRO-2H-CHROMENES -- NONSTABILIZED AZOMETHINE YLIDES -- 1,3-DIPOLAR CYCLOADDITION Аннотация: Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-α-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the Δ3-bond of the chromene system \\\\expert2\\NBO\\Tetrahedron\\2013, v. 69, p. 8602.pdf |