2909-34-4Relevant academic research and scientific papers
Sulfated tungstate: An efficient catalyst for the Ritter reaction
Katkar, Kamlesh V.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
, p. 835 - 838 (2011)
The use of sulfated tungstate as an efficient and reusable catalyst for the preparation of amides from alcohols and nitriles via the Ritter reaction pathway is discussed. The reaction proceeds under solvent free conditions. The Royal Society of Chemistry.
APPLICATIONS of ORGANOLITHIUM and RELATED REAGENTS in SYNTHESIS. Part V. Directed Metallation of Secondary Picolin- and Isonicotinamides. A Useful Method for the Synthesis of 2,3- and 3,4-Disubstituted Pyridines, Including Furopyridin-3(1H)-one and Furopyridine-1(3H)-one
Epsztajn, Jan,Bieniek, Adam,Plotka, Mieczyslaw W.
, p. 442 - 474 (2007/10/02)
The metallation reaction of N-methyl-, N-benzyl- and N-phenyl-amides (1a-c) and (2a-c) derived from picolinic and isonicotinic acids by BunLi in THF leading to the corresponding bis(N- and 3-)lithiated amides (3a-c) and (4a-c), are described.The N-phenylamides (anilides) (1c) and (2c), in comparison with the other aliphatic derivatives, demonstrate greater abilities to direct ortho lithiation at the 3-position of the pyridine ring, and give with very good yields bis(N- and 3-)lithiated anilides (3c) and (4c), respectively.The N-benzylamides (1b) and (2b) are ortho metallated under kinetic control at -78 deg C to form the bis(N- and 3-)lithiated benzylamides (3b) and (4b), but the organometallic intermediates rearrange at room temperature to give the thermodynamically more stable bis(N- and α-)lithiated amides (3g) and (4g) (benzyl-type anions).The generated carbanions (3c), (4c), (3g) and (4g) were trapped by a variety of electrophiles (e.g. alkyl halides and aldehydes).The synthesis of furopyridin-3(1H)-one (18) and furopyridin-(3H)-one (19) is included.
