A novel synthesis of diastereomerically pure spiro- oxindolopyrrolizidines and oxindolopyrrolidines via cycloaddition reactions of azomethine ylides
Journal Title: Iranian Chemical Communication - Year 2015, Vol 3, Issue 1
Abstract
An efficient one-pot three-component procedure for the synthesis of new chiral spiro oxindolopyrrolidines/pyrrolizidines with highly regio- and diastereo-enantio, selective from 1,3-dipolar cycloaddition of azomethine ylides and chiral menthol-drived trans-cinnamic are described. The mechanism of the reaction is discussed on basis of the assignment of the absolute configuration of one of the cycloaddition products, which obtained by single crystal X-ray analysis. The process occurs at reflux temperature in ethanol as green solvent and in the absence of any bidentate chelating Lewis acids. Functionalized pyrrolidines and pyrrolizidines with spirooxindole ring systems are the central skeletons for numerous alkaloids and pharmacologically important compounds.1 Gelesmine, pseudotabersonine, formosanine, isoformosanine, morroniside and mitraphylline are some of the alkaloids containing spirooxindole ring systems.
Authors and Affiliations
Mohammad Javad Taghizadeh, Khosrow Jadidi
Keywords
Related Articles
- EP ID EP258585
- DOI -
- Views 117
- Downloads 0
QSRR models of veterinary drugs in milk in ultra-performance liquid chromatography coupled to time of flight mass spectrometry
The veterinary drugs residues are also important pollutants found in milk, since veterinary drugs are commonly used in cattle management. Considering the role of milk in human nutrition and its wide consumption throughou...
Simultaneous determination of Tropaeolin O and brilliant blue in food samples after cloud point extraction
In this study, a simple and low-cost method was developed for extraction and pre-concentration of brilliant blue(BB) and Tropaeolin O(TO) in food samples using cloud point extraction (CPE) prior to spectrophotometric det...
Essential oil composition of Achillea millefolium growing in Darrehshahr township
Achillea millefolium belong to the asteraceae family and from genus achillea. In this study essential oils were extracted from all aerial parts via hydro distillation (HD) method by clevenger set . By using of gas chroma...
Development and application of a new sensitive spectrophotometric-multivariate calibration method to the simultaneous determination of hydrazine and acetylhydrazine using silver nanoparticles
In this paper, multivariate calibration methods of partial least squares (PLS) and principle component regression (PCR) were investigated in simultaneously determination of hydrazine (HZ) and acetylhydrazine (AHZ). The a...
Theoretical models for determination of weight percent of PHCS-g-PLLA co polymer using experimental data
The amphiphilic graft copolymer using chitosan (CS) as hydrophilic segment and poly (L-lactic acid) (PLLA) as hydrophobic segment, was prepared through a protection-graft-de protection route. Chitosan is a polysaccharide...