15997-45-2Relevant academic research and scientific papers
Pd(II)-Catalyzed Synthesis of Alicyclic[b]-Fused Pyridines via C(sp2)–H Activation of α,β-Unsaturated N-Acetyl Hydrazones with Vinyl Azides
Nie, Biao,Wu, Wanqing,Jin, Chuanfei,Ren, Qingyun,Zhang, Ji,Zhang, Yingjun,Jiang, Huanfeng
supporting information, p. 159 - 171 (2022/01/03)
A new synthetic protocol for alicyclic[b]-fused pyridines with complete regioselectivity from α,β-unsaturated N-acetyl hydrazones and vinyl azides via Pd(II)-catalyzed C–H activation/cyclization/aromatization strategy has been described. A series of five-
Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
Shabalin, Dmitrii A.,Dvorko, Marina Yu.,Schmidt, Elena Yu.,Trofimov, Boris A.
supporting information, p. 2703 - 2715 (2021/04/07)
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
An aminocatalyzed michael addition/Iron-Mediated decarboxylative cyclization sequence for the preparation of 2,3,4,6-Tetrasubstituted pyridines: Scope and mechanistic insights
Stivanin, Mateus L.,Duarte, Marcelo,Sartori, Camila,Capreti, Naylil M.R.,Angolini, Celio F.F.,Jurberg, Igor D.
, p. 10319 - 10330 (2018/04/20)
A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.
Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
Tan, Wei Wen,Ong, Yew Jin,Yoshikai, Naohiko
supporting information, p. 8240 - 8244 (2017/06/30)
A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.
Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
Kontokosta, Dimitra,Mueller, Daniel S.,Mo, Dong-Liang,Pace, Wiktoria H.,Simpson, Rachel A.,Anderson, Laura L.
, p. 2097 - 2104 (2016/04/01)
A Chan-Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. I
Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines
Zhu, Chunyin,Bi, Benwei,Ding, Ya,Zhang, Te,Chen, Qiu-Yun
supporting information, p. 9251 - 9257 (2015/11/27)
An iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines in one step has been developed through the green reaction system of catalytic amounts of molecular iodine and amine in combination with oxyg
Three-step synthesis of 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives
Gezegen, Hayreddin,Dingil, Alparslan,Ceylan, Mustafa
experimental part, p. 1017 - 1024 (2010/10/21)
(Chemical Equation Presented) Addition of cylohexanone to chalcones, obtained from the appropriate acetophenone and benzaldehyde derivatives, under solvent-free conditions gave 1,5-diketones in good yields. Treatment of 1,5-diketones with ammonium acetate in acetic acid afforded directly 2,4-diaryl-5,6,7,8-tetrahydroquinoline derivatives (7a-u) in high yields. The structures of 7a-u were elucidated by 1H NMR, 13C NMR, IR, and elemental analysis.
Some reactions of hexahydro[1,3,4]oxadiazolo2,3-j|quinolines and pathways of their formation
Moskovkina
, p. 1077 - 1081 (2007/10/03)
Some transformations of 2,5,7-triphenyl-7,7a,8,9,10,11-hexahydro[1,3,4]oxadiazolo[2,3-j]quino-lines and pathways of their formation by reactions of 3-(2-oxocyclohexyl)-1,3-diphenyl-1-propanone with corresponding benzohydrazides were studied. 1-Benzoylamino-2,4-diphenyl-1,4,5,6,7,8-hexahydroquinoline was prepared. In the formation of oxadiazoloquinolines from 3-(2-oxocyclohexyl)-1,3-diphenyl-1-propanone closure of the oxadiazole ring precedes closure of the quinoline system.
HYDROAMINATION OF PYRYLIUM SALTS
Kriven'ko, A. P.,Fedotova, O. V.,Reshetov, P. V.,Kharchenko, V. G.
, p. 1361 - 1364 (2007/10/02)
Some pyrylium salts and condensed systems derived therefrom have been hydromethylaminated to saturated azaheterocycles and N-methylpyridinium salts.Attempts to hydroarylaminate pyrylium salts resulted in the formation of the corresponding hydrocarbons.
THERMAL REARRANGEMENT OF PYRIDINIUM ANHYDROBASES: MIGRATION OF N-SUBSTITUENTS TO METHINE CARBON
Katritzky, Alan R.,Awartani, Radi
, p. 2505 - 2512 (2007/10/02)
N-Benzyl and N-methyl groups migrate to the methine carbon atom on thermolysis of pyridinium anhydrobases.Cross-over experiments indicate an intermolecular reaction, probably involving homolysis.
