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Selective Synthesis of 6′‐Arylidene‐1‐aryl‐3‐aryl‐spiro[pyrrolizidine‐2,2′‐cyclohexanone] by Cycloaddition of Azomethine Ylides to Dibenzylidene Cyclohexanone
Author(s) -
Gayen Biswajit,
Banerji Avijit
Publication year - 2015
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2196
Subject(s) - pyrrolizidine , chemistry , cyclohexanone , regioselectivity , cycloaddition , aryl , adduct , geotrichum , stereoselectivity , organic chemistry , medicinal chemistry , stereochemistry , catalysis , alkyl , food science
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.