ISSN:
0009-2940
Keywords:
α-Halo carbanions
;
Vicarious Nucleophilic Substitution (VNS)
;
Annulation
;
Quinoxalines
;
Naphthyridines
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Carbanions of α-haloalkyl aryl sulfones, sulfonates, and sulfonamides react with bicyclic heteroaromatic compounds (quinoxalines, naphthyridines, and 5-azaquinoxalines) according to two general pathways: vicarious nucleophilic substitution of hydrogen and/or bisannulation. In some cases other competitive reactions such as SNAr are observed. Factors governing the direction of these reactions are discussed in terms of the charge distribution in the anionic σ adducts and the reaction conditions.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240325
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