19755-53-4Relevant articles and documents
Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions
Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 5565 - 5570 (2019/10/22)
A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.
Synthesis and biological evaluation of N-arylbenzo[b]thieno[3,2-d] pyrimidin-4-amines and their pyrido and pyrazino analogues as Ser/Thr kinase inhibitors
Loidreau, Yvonnick,Marchand, Pascal,Dubouilh-Benard, Carole,Nourrisson, Marie-Renée,Duflos, Muriel,Lozach, Olivier,Loa?c, Nadège,Meijer, Laurent,Besson, Thierry
, p. 171 - 183 (2013/02/22)
A useful and rapid access to libraries of N-arylbenzo[b]thieno[3,2-d] pyrimidin-4-amines and their pyrido and pyrazino analogues was designed and optimized for the first time via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with N′-(2-cyanoaryl)-N,N- dimethylformimidamides obtained by reaction of thiophene precursors with dimethylformamide dimethylacetal. The inhibitory potency of the final products against five protein kinases (CDK5/p25, CK1δ/ε, GSK3α/β, DYRK1A and CLK1) was estimated. N-arylpyrido[3′,2′:4,5]thieno[3,2-d] pyrimidin-4-amine series of compounds (4a-j) turned out to be particularly promising for the development of new pharmacological inhibitors of CK1 and CLK1 kinases.
Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valerie,Bovy, Philippe R.,Rault, Sylvain
, p. 3323 - 3328 (2007/10/03)
This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.
