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Nitrone cycloaddition to quinones: A novel strategy for the synthesis of benzisoxazolidenes
Author(s) -
Paul Rony Rajan,
Varghese Vimal,
Beneesh P. B.,
Sinu C. R.,
Suresh E.,
Anabha E. R.
Publication year - 2010
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.255
Subject(s) - nitrone , chemistry , cycloaddition , regioselectivity , quinone , benzoquinone , 1,3 dipolar cycloaddition , photochemistry , computational chemistry , stereochemistry , organic chemistry , catalysis
1,3‐Dipolar cycloaddition reaction involving nitrones and benzoquinones resulting in the formation of benzisoxazolidene is described. As the nitrone is selectively added to carbon–carbon double bond of the benzoquinone, the quinone‐nitrone reaction is considered as a special case among quinone‐1,3‐dipole cycloaddition reactions . Molecular orbital calculation was performed to examine the electronic effects involved in the regioselectivity of the reaction. J. Heterocyclic Chem., (2010).