51640-00-7Relevant academic research and scientific papers
Mild and direct conversion of quinoline N-oxides to 2-amidoquinolines with primary amides
Couturier, Michel,Caron, Laurence,Tumidajski, Stephanie,Jones, Kris,White, Timothy D.
, p. 1929 - 1932 (2007/10/03)
A simple, one-pot procedure is described for the direct conversion of quinoline N-oxides to α-amidoquinolines with primary amides. This methodology is complimentary to the Abramovich reaction, which is limited to the introduction of secondary amides via imidoyl chlorides. Although reaction conditions are quite similar, omission of the base is key for successful reaction with primary amides, which were found not to proceed through the intermediacy of an imidoyl chloride but rather through an acyl isocyanate.
A novel three-component reaction of N-fluoropyridinium salts: A facile approach to imidazo[1,2-a]pyridines
Kiselyov, Alexander S.
, p. 4487 - 4490 (2007/10/03)
The reaction of N-fluoropyridinium triflate with isonitriles in acetonitrile and propionitrile in the presence of NaBH(OAc)3 led to the formation of the corresponding imidazo[1,2-a]pyridines in 44-73% yields. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species and apparent reduction of the pyridinium intermediate with NaBH(OAc)3 to yield the targeted heterocycles.
Carboxamidation of pyridines by the system of elemental fluorine- carbonitrile-water: A useful alternative to the chichibabin amination
Kiselyov,Strekowski
, p. 2387 - 2392 (2007/10/02)
The title reaction with pyridine, 4-methylpyridine, 3-methylpyridine, 3- bromopyridine, nicotinonitrile, and quinoline yields 2-carboxamido derivatives regioselectively. Isoquinoline is amidated at position 1.
