4706-33-6Relevant academic research and scientific papers
Direct C3 Carbamoylation of 2H-Indazoles
Bhat, Vighneshwar Shridhar,Lee, Anna
supporting information, p. 3382 - 3385 (2021/06/28)
We developed a novel method for direct C3 carbamoylation of 2H-indazoles using oxamic acids as carbamoyl radical sources. In the presence of ammonium persulfate, carbamoyl radicals were generated from oxamic acids, then used for further reactions with 2H-indazoles to afford the desired products. The reaction proceeds under metal- and catalyst-free conditions. This simple process allows for the efficient synthesis of C3 carbamoylated 2H-indazoles, which are important scaffolds in organic synthesis.
Visible-light mediated carbamoyl radical addition to heteroarenes
Jatoi, Ashique Hussain,Pawar, Govind Goroba,Robert, Frédéric,Landais, Yannick
, p. 466 - 469 (2019/01/10)
The generation of carbamoyl radicals, followed by their addition to heteroarenes, was performed under mild conditions through a metal-free photocatalyzed decarboxylation of oxamic acids. The process has been applied to the carbamoylation of heteroaromatic bases using α-aminoacid-derived oxamic acids, leading to the corresponding amides without racemization.
Metal-, Photocatalyst-, and Light-Free Direct C-H Acylation and Carbamoylation of Heterocycles
Westwood, Matthew T.,Lamb, Claire J. C.,Sutherland, Daniel R.,Lee, Ai-Lan
, p. 7119 - 7123 (2019/09/03)
Direct C-H acylations and carbamoylations of heterocycles can now be readily achieved without requiring any conventional metal, photocatalyst, electrocatalysis, or light activation, thus significantly improving on sustainability, costs, toxicity, waste, and simplicity of the operational procedure. These mild conditions are also suitable for gram-scale reactions and late-stage functionalizations of complex molecules, including pharmaceuticals, N,N-ligands, and light-sensitive molecules.
A model β-sheet interaction and thermodynamic analysis of β-strand mimetics
Robinson, Colin W.,Rye, Carl S.,Chessum, Nicola E. A.,Jones, Keith
, p. 7402 - 7407 (2015/07/15)
β-Sheet mediated protein-protein interactions are involved in key signalling pathways in diseases such as cancer. We present small molecule β-strand mimetics and investigate their interactions with a model tripeptide. Using 1H NMR, the thermodynamic parameters for their binding are determined. These give insight into this biologically important interaction.
A model β-sheet interaction and thermodynamic analysis of β-strand mimetics
Robinson, Colin W.,Rye, Carl S.,Chessum, Nicola E. A.,Jones, Keith
, p. 7402 - 7407 (2015/11/27)
β-Sheet mediated protein-protein interactions are involved in key signalling pathways in diseases such as cancer. We present small molecule β-strand mimetics and investigate their interactions with a model tripeptide. Using 1H NMR, the thermodynamic parameters for their binding are determined. These give insight into this biologically important interaction.
Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety
Liu, Zhihui,Lei, Qiong,Li, Yongqiang,Xiong, Lixia,Song, Haibin,Wang, Qingmin
experimental part, p. 12543 - 12549 (2012/03/10)
A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by 1H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.
The chemistry of vicinal tricarbonyls. Formation of oxomalondiamides
Wasserman, Harry H.,Lee, Kieseung,Xia, Mingde
, p. 2511 - 2514 (2007/10/03)
Oxomalondiamides and related systems are readily formed from derivatives of oxalic acid monoamides. The monoamides are converted to labile triacyl nitriles through cyano ylide intermediates for further coupling with amines and other nucleophiles. (C) 2000
A FACILE, CONVENIENT AND SELECTIVE HOMOLYTIC CARBAMOYLATION OF HETEROAROMATIC BASES
Coppa, Fausta,Fontana, Francesca,Lazzarini, Edoardo,Minisci, Francesco
, p. 2687 - 2696 (2007/10/02)
The oxidative decarboxylation of monoamides of oxalic acid provides carbamoyl radicals, which are useful for the selective carbamoylation of protonated heteroaromatic bases; this reaction represents the first general and selective method for the N-alkyl or N-arylcarbamoylation of heteroaromatic bases.Compared to alkoxycarbonylation, this reaction is much more effective and selective, owing to more favourable polar and enthalpic effects.The importance of the steric effects is also emphasized.
