One-pot synthesis of α-hydroxyamides using alkyl isocyanides and aryl aldehydes

Abstract

A simple and efficient approach for the synthesis of a-hydroxyamides in fairly good yields by the reaction of aromatic aldehydes and alkyl isocyanides at room temperature is presented.

Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

“…Optically active 2-hydroxyamide derivatives are frequently utilized as chiral building blocks not only for synthesizing biologically active compounds [ 1 , 2 , 3 , 4 ], but also for preparing asymmetric catalysts and chiral auxiliaries [ 5 , 6 ]. Consequently, considerable effort has been devoted toward developing efficient methods for synthesizing these compounds, including enzymatic [ 7 ] and chemical transformations [ 8 , 9 , 10 ]. For the purpose of providing chiral alcohols, the kinetic resolution (KR) of racemic alcohols by asymmetric acylation using organocatalysis is widely used as one of the most effective methods [ 11 , 12 , 13 ].…”

Novel synthesis of oxoacetamides via reaction of salicylaldehyde and isocyanide under mild reaction condition

“…On the basis of the chemistry of α-addition of aldehyde and water to isocyanide [25,26] a possible mechanism for the synthesis of the products 3a-g is proposed in Schemes 3. In the first step, it is reasonable to assume that the formation of intermediate 6 happens via the addition of salicylaldehyde 1 to isocyanide 2.…”

“…Then protonation by the H-shift occurs, and the keto-enol tautomerization followed by oxidation which results in desired product 3 (Scheme 3). It is expected that oxygen in the airflow or one of the substances in the reaction act as an oxidizer, but based on the previous works [25,26] the hydroxy group on aromatic moiety is likely to be effective in oxidizing of benzylic hydroxyl group. Apparently, the hydroxy group in the oxidation process, by transferring electrons to ortho-carbon, enriches the electron cloud of the benzyl position and facilitates the process of oxidation of the benzylic hydrogen.…”

“…Although, published papers in recent years show various protocols for the synthesis of products with analogous structures but introduce of an efficient and practical procedure for the synthesis of these pharmaceutical compounds from commercial chemicals is still seems essential. In the following of our research interests in isocyanide reactions [24,25], we would like to report here a new and atomic economic process for the synthesis of oxoacetamides via reaction of salicylaldehyde and isocyanide under mild reaction condition.…”

Kinetic Resolution of Racemic 2-Hydroxyamides Using a Diphenylacetyl Component as an Acyl Source and a Chiral Acyl-Transfer Catalyst

“…Optically active 2-hydroxyamide derivatives are frequently utilized as chiral building blocks not only for synthesizing biologically active compounds [1][2][3][4] but also for preparing asymmetric catalysts and chiral auxiliaries [5][6]. Consequently, considerable effort has been devoted toward developing efficient methods for synthesizing these compounds, including enzymatic [7] and chemical transformations [8][9][10]. However, to the best of our knowledge, a general method for the kinetic resolution (KR) of racemic 2-hydroxyamide derivatives has not been reported to date.…”