Synthesis of the (2S,4S)-stereoisomers of 4-(indol-1-yl) and 4-arylamino derivatives of 5-oxoproline, proline, and 2-hydroxymethylpyrrolidine / Vigorov A. Yu,Nizova I. A.,Shalunova K. E.,Grishakov A. N.,Sadretdinova L. Sh,Ganebnykh I. N.,Ezhikova M. A.,Kodess M. I.,Krasnov V. P. // RUSSIAN CHEMICAL BULLETIN. - 2011. - V. 60, l. 5. - P. 873-881.

ISSN/EISSN:

1066-5285 / 1573-9171

Type:

Article

Abstract:

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.

Author keywords:

4-aminoproline; glutamic acid; indole; 5-oxoproline; proline; prolinol PYROGLUTAMIC ACID; 4-AMINO DERIVATIVES; INDOLE-DERIVATIVES; INHIBITORS; ESTERS

DOI:

10.1007/s11172-011-0137-4

Web of Science ID:

ISI:000297153800013

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	MAY
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-9171
Keywords-Plus	PYROGLUTAMIC ACID; 4-AMINO DERIVATIVES; INDOLE-DERIVATIVES; INHIBITORS; ESTERS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	ca@ios.uran.ru
Funding-Acknowledgement	Ural Branch of the Russian Academy of Sciences {[}09-P-3-2001, 09-I-3-2004]; Council on Grants at the President of the Russian Federation {[}NSh-65261.2010.3]
Funding-Text	This work was financially supported by the Ural Branch of the Russian Academy of Sciences (Project Nos 09-P-3-2001 and 09-I-3-2004), the Youth Competitive Project of the Ural Branch of the Russian Academy of Sciences, and the Council on Grants at the President of the Russian Federation (State Support Program for Leading Scientific Schools of the Russian Federation, Grant NSh-65261.2010.3).
Number-of-Cited-References	31
Usage-Count-Since-2013	2
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	849VQ