 A high-yielding, multi-gram synthesis of vinamidinium salts 1  is described. These compounds are easily handled, hydrolytically stable, crystalline solids conveniently isolated as their hexafluorophosphate salts. An X-ray structure is reported, and the bond distances therein suggest that the charge is distributed similarly among the two nitrogen atoms. An efficient one-pot conversion of 1  to 2-aminoquinolines 2  via cyclocondensation with anilines is described. This process makes available a variety of 5-, 6-, 7-, and 8-substituted 2-aminoquinolines. Employing allyl substituents as R1 and R2 allows access to the parental 2-aminoquinolines by straightforward deprotection using palladium catalysis.

Preparation and utility of vinamidinium salts as precursors to 2-aminoquinolines

245th National Meeting (2013)

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