30489-43-1Relevant academic research and scientific papers
KIO4-mediated Selective Hydroxymethylation/Methylenation of Imidazo-Heteroarenes: A Greener Approach
Braga, Antonio Luiz,Franco, Marcelo Straesser,Rafique, Jamal,Saba, Sumbal
supporting information, p. 18454 - 18460 (2021/07/21)
Herein, we report a KIO4-mediated, sustainable and chemoselective approach for the one-pot C(sp2)?H bond hydroxymethylation or methylenation of imidazo-heteroarenes with formaldehyde, generated in situ via the oxidative cleavage of ethylene glycol or glycerol (renewable reagents) through the Malaprade reaction. In the presence of ethylene glycol, a series of 3-hydroxymethyl-imidazo-heteroarenes was obtained in good to excellent yields. These compounds are important intermediates to access pharmaceutical drugs, e.g., Zolpidem. Furthermore, by using glycerol, bis(imidazo[1,2-a]pyridin-3-yl)methane derivatives were selectively obtained in good to excellent yields.
Umpolung of protons from H2O: A metal-free chemoselective reduction of carbonyl compounds: Via B2pin2/H2O systems
Xuan, Qingqing,Zhao, Cong,Song, Qiuling
supporting information, p. 5140 - 5144 (2017/07/11)
H2O is routinely described as a proton donor, however, in the presence of diboron compounds, the umpolung reaction of H2O under metal-free conditions was successfully developed, which could afford hydride species, leading to a highly efficient and chemoselective reduction of CO bonds. This strategy exhibits excellent chemoselectivities toward carbonyl groups in the presence of ester, olefin, halogen, thioether, sulfonyl, cyano as well as heteroaromatic groups.
Silver-catalyzed cyclization of N-(prop-2-yn-1-yl)pyridin-2-amines
Chioua, Mourad,Soriano, Elena,Infantes, Lourdes,Jimeno, M. Luisa,Marco-Contelles, Jose,Samadi, Abdelouahid
, p. 35 - 39 (2013/02/22)
We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl)pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines. The isomerization reactions proce
Synthesis of imidazo[1,2-a]pyridines: "Water-mediated" hydroamination and silver-catalyzed aminooxygenation
Chandra Mohan, Darapaneni,Nageswara Rao, Sadu,Adimurthy, Subbarayappa
supporting information, p. 1266 - 1272 (2013/08/24)
Aqueous syntheses of methylimidazo[1,2-a]pyridines without any deliberate addition of catalyst are reported. Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yields under similar conditions. With acetonitrile as solvent, Ag
Synthesis, stereochemistry and SAR of a series of minodronate analogues as RGGT inhibitors
B?aewska, Katarzyna M.,Ni, Feng,Haiges, Ralf,Kashemirov, Boris A.,Coxon, Fraser P.,Stewart, Charlotte A.,Baron, Rudi,Rogers, Michael J.,Seabra, Miguel C.,Ebetino, Frank H.,McKenna, Charles E.
experimental part, p. 4820 - 4826 (2011/11/13)
Phosphonocarboxylate (PC) analogues of bisphosphonates are of interest due to their selective inhibition of a key enzyme in the mevalonate pathway, Rab geranylgeranyl transferase (RGGT). The dextrarotatory enantiomer of 2-hydroxy-3-(imidazo[1,2-a]pyridin-3-yl)-2-phosphonopropanoic acid (3-IPEHPC, 1) is the most potent PC-type RGGT inhibitor thus far identified. The absolute configuration of (+)-1 in the active site complex has remained unknown due to difficulties in obtaining RGGT inhibitor complex crystals suitable for X-ray diffraction analysis. However, we have now succeeded in crystallizing (-)-1 and here report its absolute configuration (AC) obtained by X-ray crystallography, thus also defining the AC of (+)-1. An Autodock Vina 1.1 computer modeling study of (+)-1 in the active site of modified RGGT binding GGPP (3DSV) identifies stereochemistry-dependent interactions that could account for the potency of (+)-1 and supports the hypothesis that this type of inhibitor binds at the TAG tunnel, inhibiting the second geranylgeranylation step. We also report a convenient 31P NMR method to determine enantiomeric excess of 1 and its pyridyl analogue 2, using α- and β-cyclodextrins as chiral solvating agents, and describe the synthesis of a small series of 1 α-X (X = H, F, Cl, Br; 7a-d) analogues to assess the contribution of the α-OH group to activity at enzyme and cellular levels. The IC50 of 1 was 5-10× lower than 7a-d, and the LED for inhibition of Rab11 prenylation in vitro was 2-8× lower than for 7a-d. However, in a viability reduction assay with J774 cells, 1 and 7b had similar IC50 values, ～10× lower than those of 7a and 7c-d.
Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents
Gueiffier, Alain,Lhassani, Mohammed,Elhakmaoui, Ahmed,Snoeck, Robert,Andrei, Graciela,Chavignon, Olivier,Teulade, Jean-Claude,Kerbal, Abdelali,Essassi, El Mokhtar,Debouzy, Jean-Claude,Witvrouw, Myriam,Blache, Yves,Balzarini, Jan,De Clercq, Erik,Chapat, Jean-Pierre
, p. 2856 - 2859 (2007/10/03)
The synthesis and the antiviral activities of C-3 acyclic nucleoside analogues of imidazo[1,2-a]pyridine and pyrimidine are reported. From these compounds, 20, 21, 22, 23, 28, and 34 showed a specific activity against cytomegalovirus and/or varicella-zoster virus.
C-3 Hydroxylation of Some Imidazoazines
Teulade, Jean C.,Bonnet, Pierre A.,Rieu, Jean N.,Viols, Henry,Chapat, Jean P.,et al.
, p. 1842 - 1874 (2007/10/02)
Reactions of imidazopyridine, pyrimidine and pyrazine (1)-(3) with formaldehyde or acetaldehyde give the corresponding alcohols and secondary products characterized by 1H and 13C n.m.r.X-Ray crystallographic analysis confirms the structure of (6).The two-step sequence of n-butyllithium and reaction with aldehydes with (2)-(3) does not lead to the alcohols but to n-butyl derivatives with substituents at C(7) and C(8) respectively.
