106590-23-2Relevant academic research and scientific papers
Divergent Palladium-Catalyzed Tandem Reaction of Cyanomethyl Benzoates with Arylboronic Acids: Synthesis of Oxazoles and Isocoumarins
Chen, Jiuxi,Chen, Zhongyan,Dai, Ling,Shao, Yinlin,Xiong, Wenzhang,Xu, Tong,Yu, Shuling
supporting information, (2020/04/15)
A palladium-catalyzed tandem reaction of cyanomethyl benzoates with arylboronic acids has been achieved. Substitution at the 2-position of cyanomethyl benzoates was found to be crucial for the selective synthesis of oxazoles and isocoumarins. Cyanomethyl
Synthesis of 2,4,5-Trisubstituted Oxazoles via Pd-Catalyzed C-H Addition to Nitriles/Cyclization Sequences
Zhang, Di,Song, Hao,Cheng, Na,Liao, Wei-Wei
supporting information, p. 2745 - 2749 (2019/04/30)
A practical and flexible intermolecular protocol for the diverse synthesis of trisubstituted oxazole derivatives via a Pd-catalyzed direct C-H addition of electronic-rich heteroarenes to O-acyl cyanohydrins bearing an α-hydrogen/cyclization sequence is described. A wide range of trisubstituted oxazoles can be prepared from readily available starting materials in good to high yields with high efficiency under redox neutral reaction conditions.
DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride
Poisson, Thomas,Dalla, Vincent,Papamica?l, Cyril,Dupas, Georges,Marsais, Francis,Levacher, Vincent
, p. 381 - 386 (2008/01/08)
A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.
Solvent-free synthesis of cyanohydrin derivatives catalysed by triethylamine
Baeza, Alejandro,Najera, Carmen,Retamosa, Ma. De Gracia,Sansano, Jose M.
, p. 2787 - 2797 (2007/10/03)
A very simple one-step environmentally friendly procedure for the synthesis of O-substituted cyanohydrins from aldehydes and ketones, in the absence of solvent, employing minimum amounts of the corresponding cyanides has been optimised. Aldehydes react more rapidly than ketones using triethylamine as catalyst offering in both cases almost quantitative yields of the corresponding O-trimethylsilyl, O-methoxycarbonyl, O-benzoyl and O-acetyl cyanohydrins. Georg Thieme Verlag Stuttgart.
DABCO-Mediated Synthesis and Biological Activity of Cyanihydrin Esters
Hoffmann, H. M. R.,Ismail, Z. M.,Hollweg, Reiner,Zein, Abdul R.
, p. 1807 - 1810 (2007/10/02)
Cyanohydrin esters 1-31 have been prepared from α-ketonitriles and aldehydes using DABCO (1,4-diazabicyclooctane) as nucleophilic acylation catalyst.The modofied piperonal 8 was found to inhibit the formation of thromboxane synthetase.
