Direct diastereoselective introduction of l-menthol residue into 1,2,4-triazin-5(4H)-one / Zyryanov GV,Rusinov VL,Chupakhin ON,Krasnov VP,Levit GL,Kodess MI,Shtukina TS // RUSSIAN CHEMICAL BULLETIN. - 2004. - V. 53, l. 6. - P. 1290-1294.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

The reaction of 3-phenyl-1,2,4-triazin-5 (4H)-one (1) with l-menthol in the presence of aliphatic acid anhydrides results in (6S)- and (6,R)-1-acyl-6-(1-menht-3-yl)-1,6-dyhydro-3phenyl- 1, 2,4-triazin-5(4H)-ones. The reaction is diastereoselective with predominant formation of (6S)-isomers. The reaction diastereoselectivity increases with enhancement of the steric hindrance in the vicinity of the reaction center of the azine.

Author keywords:

3-phenyl-1,2,4-triazin-5(4H) -one; l-menthol; diastereoselectivity; acetic anhydride; isobutyric anhydride; 1-acyl-6-(l-menth-3-yloxy)-3-phenyl-1,6 dyhydro-1,2,4-triazin-5 (4H) -ones; nucleophilic add CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS; ENANTIOPURE N-ACYLDIHYDROPYRIDONES; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES

DOI:

10.1023/B:RUCB.0000042288.9150

Web of Science ID:

ISI:000224147800023

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	CONSULTANTS BUREAU
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS; ENANTIOPURE N-ACYLDIHYDROPYRIDONES; ASYMMETRIC-SYNTHESIS; GRIGNARD-REAGENTS; 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	ca@ios.uran.ru rusinov@htf.ustu.ru
Number-of-Cited-References	16
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	857VR