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Synthesis of Heterocycles by Intramolecular Nucleophilic Substitution at an Electron‐Deficient sp 2 Nitrogen Atom
Author(s) -
Sączewski Jarosław,
Gdaniec Maria
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901520
Subject(s) - chemistry , nucleophilic substitution , nucleophile , intramolecular force , medicinal chemistry , sulfur , substitution reaction , sulfonate , intramolecular reaction , nitrogen , imidazolidine , leaving group , stereochemistry , organic chemistry , catalysis , sodium
2‐Aryl(arylsulfonyl)‐6,7‐dihydro‐2 H ‐imidazo[2,1‐ c ][1,2,4]triazol‐3(5 H )‐ones and 3‐arylimino‐6,7‐dihydroimidazo[2,1‐ c ][1,2,4]thiadiazoles have been synthesized by intramolecular nucleophilic substitution reactions at the electron‐deficient sp 2 nitrogen atom of 2‐(hydroxyimino)imidazolidine O ‐sulfonate. The displacement of the sulfate leaving group by both nitrogen and sulfur anionic nucleophiles proceeds exothermically by in‐plane S N 2σ nucleophilic substitution.
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