55249-89-3Relevant articles and documents
Lewis acid-promoted direct substitution of 2-methoxy-3-cyanopyridines by organo cuprates. Part 3: Facile preparation of nicotinamide and nicotinic acid derivatives
Abdel-Aziz, Alaa A.-M.
, p. 2861 - 2865 (2007)
2-Methoxy-3-cyano-4,6-diarylpyridines were subjected to Lewis acid-promoted nucleophilic displacement reactions with various organo cuprates to afford the corresponding 2,4,6-trisubstituted nicotinonitriles. Subsequent hydrolysis of compounds 10 and 11 af
Pyridine Syntheses. II. Condensation Routes Toward Streptonigrin Ring C [1]
Robinson, J. Michael,Ahmed, Masood,Alaniz, Nicky J.,Boyles, Timothy P.,Brasher, Chris D.,Floyd, Kimberly A.,Holland, Preston L.,Maruffo, Laura D.,McMahan, Terry L.,Middleton, Stan,O'Hara, Kevin D.,Pack, Marcia J.,Reynolds, Brandon D.,Rodriquez, Romelia R.,Sawyer, Dennis E.,Sharp, Elena,Simpson, Sharai L.,Vanlandingham, Clint L.,Velasquez, Rebecca S.,Welch, Brian M.,Wright, C. David
, p. 65 - 69 (2007/10/03)
Alternative complimentary syntheses of penta-substituted pyridine rings with full regiochemical control of substituents were studied as a method for the synthesis of Streptonigrin (1). Various α-substituted acetophenones 2 were reacted with enones 3 in acetic acid/ammonium acetate and air to afford penta-substituted pyridines 4. α-Substituents that could provide a source of exocyclic nitrogen at position 3 of these Steptonigrin ring-C models proved to be the limiting factor. However, an inverse "3+2+1" cyclocondensation of α-cyanochalcone 5c with 2-furyl ethyl ketone (6b) afforded the desired model 6-(2-furyl)-5-methyl-2,4-diphenyl-3-pyridinecarbonitrile (4g) in 75% yield.
PREPARATION AND REACTIONS OF 1-CYANOMETHYL-2,4,6-TRISUBSTTUTED PYRIDINIUM YLIDS
Katritzky, Alan R.,Yeung, Wing Kai,Patel, Ranjan C.,Burgess, Kevin
, p. 623 - 632 (2007/10/02)
Aminoacetonitrile with pyrylium forms pyridiniums which are acylated to solvatochromic ylids.Pyrolysis of ylid (10a) (R=p-toluoyl) gives 3-cyano-2,4,6-triphenylpyridine. 1-Cyanomethyl-pyridinium (6) gives tetrahydroindolizines with α,β-unsaturated carbonyl compounds.
