6948-58-9Relevant academic research and scientific papers
Synthesis of Imidazoles and Oxazoles via a Palladium-Catalyzed Decarboxylative Addition/Cyclization Reaction Sequence of Aromatic Carboxylic Acids with Functionalized Aliphatic Nitriles
Dai, Ling,Yu, Shuling,Lv, Ningning,Ye, Xuanzeng,Shao, Yinlin,Chen, Zhongyan,Chen, Jiuxi
supporting information, p. 5664 - 5668 (2021/08/01)
We herein report an efficient approach for the assembly of multiply substituted imidazoles and oxazoles in a single-step manner. These transformations are based on a decarboxylation addition and annulation of readily accessible aromatic carboxylic acids a
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
One-Pot Three-Component Solvent-Free Cyanoaroylation of Aldehydes Using Potassium Hexacyanoferrate(II) as an Environmentally Benign Cyanide Source
Li, Zheng,Tian, Guoqiang,Ma, Yuanhong
supporting information; experimental part, p. 2164 - 2168 (2010/10/21)
An efficient method for one-pot three-component solvent-free cyanoaroylation of aldehydes using potassium hexacyanoferrate(II) as an environmentally benign cyanide source and triethylamine as a catalyst has been described. This method has advantages of not using strongly toxic cyanating agents and volatile organic solvents. In addition, the product was obtained in high yield using a simple workup procedure.
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.
A convenient and improved method for the preparation of cyanohydrin esters from acyl cyanides and aldehydes
Okimoto, Mitsuhiro,Chiba, Toshiro
, p. 1188 - 1190 (2007/10/03)
Various kinds of cyanohydrin esters can be obtained in good to excellent yields from aldehydes by treatment with acyl cyanides in a heterogeneous mixture of aqueous potassium carbonate and acetonitrile.
A Simple One-Pot Synthesis of Silylated and Acylated Cyanohydrins
Yoneda, Ryuji,Santo, Kazunori,Harusawa, Shinya,Kurihara, Takushi
, p. 1054 - 1055 (2007/10/02)
Reaction of variety of aldehydes and ketones with chlorotrimethylsilane and acyl chlorides in the presence of lithium cyanide to give trimethylsilylcyanohydrins and acylcyanohydrins is described.
CYANOHYDRINS AS SUBSTRATES IN BENZOIN CONDENSATION. REGIOCONTROLLED MIXED BENZOIN CONDENSATION
Rozwadowska, Maria D.
, p. 3135 - 3140 (2007/10/02)
O-Benzoylated cyanohydrins of aromatic aldehydes have been used as one of the substrates in the benzoin condensation.They were treated with aromatic aldehydes under phase-transfer conditions to result in benzoin benzoates.By this method aldehydes which fail to undergo condensation using traditional conditions could be converted into benzoins.By the Umpolung of reactivity of the pertinent aldehyde it was possible to prepare both isomeric unsymmetrical benzoins, including the thermodynamically less stable ones.
CROWN ETHER CATALYSIS IN THE SYNTHESIS OF CYANOHYDRIN DERIVATIVES
Chenevert, Robert,Plante, Raymond,Voyer, Normand
, p. 403 - 410 (2007/10/02)
Carbonyl compounds react with cyanide ion under phase transfer catalysis (18-crown-6) to give cyanohydrin anions which are trapped by acid chlorides, anhydrides or alkylating agents to give cyanohydrin derivatives.
