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Regioselective Cyclizations of Delocalized 1,3‐Amide Dianions with Oxalic Acid Dielectrophiles
Author(s) -
Langer Peter,
Döring Manfred,
Görls Helmar,
Beckert Rainer
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971220
Subject(s) - regioselectivity , chemistry , tautomer , oxalic acid , amide , delocalized electron , nitrogen , organic chemistry , catalysis
A novel strategy for the synthesis of nitrogen‐rich heterocycles by regioselective C,N‐cyclization of ambident dianions with oxalimidoyl dichlorides is reported. One ‐ pot reactions provide γ‐iminotetramic acid amides 1 , radialenes 2 and tetraimino‐diazaspiro[4.4]nonenones 3 . Chemical properties and structural features of the new heterocyclic systems, including the tautomerism of 2 , were investigated.
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