Optically active imidazole N-oxides derived from l-prolinamine1
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چکیده
منابع مشابه
Synthesis of new optically active polycyclic N-heterocycles derived from L- prolinamine
The N-Boc-protected (S)-prolinamine reacts readily with formaldehyde and diverse alphahydroxyimino ketones to give imidazole N-oxides with an enantiomerically pure N-protected (pyrrolidin-2yl)methyl substituent. Subsequent deprotection yields the corresponding NH derivatives. Upon treatment of these products with Ac2O at room temperature, a cascade of reactions leads to optically active tricycl...
متن کاملFacile synthesis of optically active imidazole derivatives.
Five optically active imidazole derivatives have been synthesized via a facile 4-step reaction sequence starting from commercially available and inexpensive N-Cbz amino acids. While microwave assisted condensation was unsuccessful, the condensation of the corresponding alpha-bromoketones with formamidine acetate in liquid ammonia was revealed to be a useful method for the synthesis of such imid...
متن کاملOnes, thiones, and N-oxides: an exercise in imidazole chemistry.
General Procedure: 1-Propylimidazole-N-oxide (2a) 1 (1.0 g, 4.1 mmol) and 1,3,5-tripropylhexahydro-1,3,5triazine (0.5 g, 2.4 mmol) were dissolved in ethanol (20 mL). The reaction mixture was heated to reflux for 10 h. The light brown solution was cooled to room temperature and the solvent removed under reduced pressure. The oily residue solidified upon trituration with diethylether to give 2a a...
متن کاملNew Optically Active Bis-Heterocycles Derived from (S)-Proline
Enantiomerically pure bis-heterocycles containing a (S)-proline moiety have been prepared starting from (S)-N-benzylprolinehydrazide (2b). The reactions with isothiocyanates or butyl isocyanate in refluxing MeOH led to the corresponding thiosemicarbazide 5 and semicarbazide 9 with a N-benzylprolinoyl residue. The structure of the tert-butyl derivative 5d was established by X-ray crystallography...
متن کاملChiral Imidazoles and Imidazole N-Oxides as Ligands for Stereoselective Cyclopropanation reactions
New, optically active ligands derived from imidazole were tested in the cyclopropanation reaction of styrene using ethyl diazoacetate and copper(I) triflate as a catalyst. DOI: https://doi.org/10.2174/157017812800221735 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-61481 Accepted Version Originally published at: Mloston, G; Mucha, P...
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ژورنال
عنوان ژورنال: Tetrahedron: Asymmetry
سال: 2013
ISSN: 0957-4166
DOI: 10.1016/j.tetasy.2013.07.013