402567-85-5Relevant academic research and scientific papers
On-Water Cp?Ir(III)-catalyzed C-H functionalization for the synthesis of chromones through annulation of salicylaldehydes with diazo-ketones
Debbarma, Suvankar,Sk, Md Raja,Modak, Biswabrata,Maji, Modhu Sudan
, (2019/05/22)
A high-valent Ir(III)-catalyzed C-H bond functionalization is carried out for the first time on water for the synthesis of a biologically relevant chromone moiety. The C-H activation and annulation of salicylaldehydes with diazo-compounds provided the desired chromones. The synthesis of C3-substitution-free chromones has also been demonstrated by a one-pot decarboxylation by employing tert-butyl diazoester. C3 and C5 C-H activations of the product chromone are also carried out under different conditions for further diversification.
Nucleophilic fluorination of β-ketoester derivatives with HBF 4
Pasceri, Raffaele,Bartrum, Hannah E.,Hayes, Christopher J.,Moody, Christopher J.
supporting information, p. 12077 - 12079 (2013/01/16)
Treating readily available α-diazo-β-ketoesters with HBF 4 results in nucleophilic fluorination by the usually inert and stable tetrafluoroborate anion. The resulting α-fluoro-β-ketoesters are highly versatile synthetic intermediates, for example in the preparation of fluoro-heterocycles, as illustrated by the direct formation of fluoro-pyrimidines, -pyrazoles and -coumarins in a single step.
A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters
Li, Puhui,Majireck, Max M.,Korboukh, Ilia,Weinreb, Steven M.
, p. 3162 - 3164 (2008/09/20)
A wide variety of α-diazo-β-ketoesters can be prepared in good overall yields via a two-step sequence involving addition of ethyl lithiodiazoacetate to aliphatic, aromatic, and conjugated aldehydes followed by mild oxidation with the Dess-Martin periodina
Metalation of α-diazocarbonyl compounds using Grignard reagents. A convenient synthesis of α-diazo-β-ketoesters and mixed esters of α-diazomalonate
Cuevas-Ya?ez, Erick,Muchowski, Joseph M.,Cruz-Almanza, Raymundo
, p. 2417 - 2419 (2007/10/03)
α-Diazocarbonyl compounds react with methylmagnesium bromide at -78°C generating the corresponding α-diazo-α-bromomagnesio species, which can be intercepted by various electrophilic reagents. For example, with alkyl chloroformates α-diazo-β-ketoesters or mixed esters of α-diazomalonate are obtained in good yields.
