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Reaction of Ambident Dianions with Oxalic Acid Dielectrophiles – Effect of the Heteroatoms of the Dinucleophile on the Regiochemistry of Cyclization
Author(s) -
Langer Peter,
Wuckelt Jörg,
Döring Manfred,
Beckert Rainer
Publication year - 1998
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/(sici)1099-0690(199807)1998:7<1467::aid-ejoc1467>3.0.co;2-h
Subject(s) - chemistry , heteroatom , oxalic acid , regioselectivity , reagent , medicinal chemistry , organic chemistry , catalysis , ring (chemistry)
Abstract Y‐Shaped ambident dianions 1‐6 were reacted with dielectrophilic oxalic acid‐bis(imidoyl)dichlorides 7 providing a convenient access to novel N‐heterocycles 8‐13 containing a heteroanalogous oxalic acid unit. The cyclization reactions generally proceeded with good regioselectivity which is controlled by the heteroatoms of the dianion reagents.