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1,3‐Dipolar Cycloaddition Reactions Leading to the Synthesis of New 2,3,5‐Triaryl‐4 H ,2,3,3a,5,6,6a‐hexahydropyrrolo[3,4‐ d ]isoxazole‐4,6‐diones
Author(s) -
Kaur Anjandeep,
Singh Baldev
Publication year - 2014
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.1838
Subject(s) - chemistry , cycloaddition , isoxazole , nitrone , maleimide , steric effects , substituent , selectivity , ring (chemistry) , stereochemistry , proton nmr , 1,3 dipolar cycloaddition , diastereomer , aryl , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , catalysis , alkyl
Cycloaddition of C , N ‐diphenylnitrones 1 to N ‐aryl maleimides 2 afforded two diastereomeric isoxazolidines with high selectivity. The structure and steric configuration of the adducts have been assigned on the basis of 1 H NMR, 1 H NMR COSY, 13 C NMR and IR spectroscopy. The π–π stacking interactions between maleimide's and nitrone's aromatic rings during the 1,3‐dipolar cycloaddition were assumed to control the exo–endo selectivity of the reaction. Thus, the exo–endo ratio depends upon the position of the substituent present on the C ‐phenyl ring of the C , N ‐diphenylnitrones.