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Publikācija: Resolution

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language Resolution, Absolute Configuration, and Synthetic Transformations of 7-Amino-Tetrahydroindazolones
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Inta Strakova
Ilze Kumpiņa
Vitālijs Rjabovs
Jevgeņija Lugiņina
Sergejs Beļakovs
Māris Turks
Keywords Tetrahydroindazolones, chiral resolution, X-ray studies
Abstract The chiral resolution of 7-amino-1-aryl-4,5,6,7-tetrahydro-indazol-4-ones was achieved via salt formation with O,O′-dibenzoyl tartaric acid. The transformation of enantiomerically enriched 7-amino-THIs into their corresponding azides proceeds with no decrease in their ee’s. A comparison of the X-ray structures of the racemic and enantiopure forms of the title compounds explains the rather large melting point differences between both the series. The enantiopure azides obtained from the corresponding 7-amino-THIs were employed in copper-catalyzed Huisgen 1,3-dipolar cycloaddition reactions with various alkynes. The use of enantiomerically enriched THI scaffolds is demonstrated by the preparation of diastereomerically pure products when the former are conjugated with alkynes arising from natural sources.
DOI: 10.1016/j.tetasy.2011.03.010
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0957416611001662 
Reference Strakova, I., Kumpiņa, I., Rjabovs, V., Lugiņina, J., Beļakovs, S., Turks, M. Resolution, Absolute Configuration, and Synthetic Transformations of 7-Amino-Tetrahydroindazolones. Tetrahedron: Asymmetry, 2011, Vol.22, Iss.7, pp.728-739. ISSN 0957-4166. Available from: doi:10.1016/j.tetasy.2011.03.010
Additional information Citation count:
ID 10647