65321-29-1Relevant articles and documents
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
Ishii, Takuya,Kakeno, Yuki,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information, p. 3854 - 3858 (2019/04/25)
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.
Enantioselective Synthesis of Optically Active Pyridine Derivatives and C2-Symmetric 2,2'-Bipyridines
Bolm, Carsten,Ewald, Martina,Felder, Marcel,Schlingloff, Gunther
, p. 1169 - 1190 (2007/10/02)
Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11-13, 24, and 25 using the chiral borane reagent chlorodiisopinocampherylborane .Nickel(0)-mediated coupling of bromopyridines 2, 15, and 31 gives C2-symmetric 2,2'-bipyridines (R,R)-32, (R,R)-33, and (S,S)-38, respectively, which form metal complexex with Co(II), Pd(II), Cu(I), and Ag(I).Aryl-substituted pyridines 26, and 39-41 are synthesized by palladium(0)-catalized cross coupling of 2 and 15 with boronic acids 42-44.Key Words: 2,2-Bipyridines / Pyridines, optically active / Chiral ligands / Asymmetric Synthesis / Catalysis, enantioselective
Fungicidal Pyridine Derivatives I: α-Trichloromethyl-3-pyridinemethanols
Sauter, Fritz,Stanetty, Peter,Sittenthaler, Wilhelm,Waditschatka, Rudolf
, p. 1427 - 1438 (2007/10/02)
The title substances, a new type of compounds with fungicidal activity, were synthesized by addition of trichloromethyllithium (and tribromomethyllithium resp.) to various 3-pyridyl ketones at -100 deg C. - Keywords: Fungicides; Pyridinemethanoles; Trichl
Cyclising Nucleophilic Addition to Azinium Systems. Part 2. Reactions of 3-Acylpyridinium Hydrazones.
Street, Jonathan D.,Baradarani, M. Mehdi,Beddoes, Roy L.,Mills, Owen S.,Joule, John A.
, p. 1247 - 1285 (2007/10/02)
3-Acyl-1-methylpyridinium tosyl- and benzoylhydrazines lose a side-chain N-hydrogen on treatment with mild base thus forming zwitterions, isolable in some cases; intramolecular nucleophilic cyclising addition to the pyridinium nucleus in these was observe
Some reactions of 3-cyano(diethylaminocarbonyl, methoxycarbonyl) pyridines with organolithium reagents. Synthesis of stabilized 1,2-, 1,4-, and 1,6-dihydropyridines
Din, M. Gamal El,Knaus, Edward E.,Giam, Choo-Seng
, p. 1821 - 1827 (2007/10/02)
The reaction of 3-cyano 5a, 3-diethylaminocarbonyl 5b, and 3-methoxycarbonylpyridine 5c with alkyllithiums 6 has been investigated as a method of preparing stable dihydropyridines.Reaction of 5a with 6 affords a mixture of 1,2- and 1,6-dihydropyridines 10 and 11, whereas reaction of 5b and 5c with 6 yields a mixture of 1,4- and 1,6-dihydropyridines 11 and 12.The cyano and diethylaminocarbonyl substituents of 5a and 5b are relatively resistant toward attack by the alkyllithium whereas reaction of the methoxycarbonyl substituent of 5c is competitive with addition to the ring.The stabilities of the dihydropyridines prepared are described.