Selective Synthesis of 6′-Arylidene-1-aryl-3-aryl-spiro[pyrrolizidine-2,2′-cyclohexanone] by Cycloaddition of Azomethine Ylides to Dibenzylidene Cyclohexanone

Autor:	Avijit Banerji, Biswajit Gayen
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Spiro compound Double bond Aryl Organic Chemistry Azomethine ylide Cyclohexanone Medicinal chemistry Cycloaddition chemistry.chemical_compound chemistry 1 3-Dipolar cycloaddition Pyrrolizidine Organic chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 52:919-925
ISSN:	0022-152X
DOI:	10.1002/jhet.2196
Popis:	Azomethine ylides derived in situ from l-proline and aryl aldehydes underwent regioselective and stereoselective cycloadditions with diaryl cycloahexanone to form a series of spiro-pyrrolizidine compounds. By using equimolar proportions of the reactants in DMF, only a single mono-adduct, namely 6′-arylidene-1-aryl-3-aryl-spiro[pyrrolizidine-2,2′-cyclohexanone], was formed, the second double bond in the dipolarophile remaining unaffected. Structure elucidation was achieved by detailed spectroscopic analyses and XRD studies. Interesting solid-state structural characteristics were revealed by XRD analysis.
Databáze:	OpenAIRE
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