N,N-Dicarboxymethyl hydrazine: an old but neglected reagent for chemoselective derivatization of carbonyl compounds

Abstract

N,N-Dicarboxymethyl hydrazine (DCMH) was found to be a chemoselective derivatization reagent of carbonyl compounds and its potential applications in organic synthesis was investigated for the first time. DCMH could be employed as a chemoselective protective reagent of aldehydes and gave the parent aldehydes in satisfactory yields. In proof-of-concept systems, DCMH could play the role of a scavenger to remove aldehydes in the presence of ketones. It was also used as a tagging reagent in the selective isolation of aldehyde from the complex mixture.

Coumarin‐Chalcones Generated from 3‐Acetylcoumarin as a Promising Agent: Synthesis and Pharmacological Properties

“…3-Acetylcoumarin (2) are used in different reactions for preparation of chalcone compounds. for instance, the con-densation of 3-acetylcoumarin (2) and variant aldehydes (3) results in a series of chalcone derivatives (4) in reasonable-toexcellent yields through a Claisen-Schmidt condensation reaction [42] that is catalyzed by various bases (piperidine; [43,44,53,54,[45][46][47][48][49][50][51][52] morpholine; [55,56] sodium hydroxide; [57][58][59] potassium hydroxide [60,61] in PEG-400; [62] pyrrolidine [63] ) and acids (acetic acid; [64] concentrated sulfuric acid; [65] para-toluene sulfonic acid; [66] silica sulfuric acid under solvent-free conditions [67] and under microwave irradiation [38,[68][69][70] ); a mixture of piperidine and acetic acid in n-butanol; [71,72] or in ethanol [73] (Scheme 2). The mixture is cooled to room temperature when Scheme 5.…”

Ultrasound assisted eco-friendly synthesis of 3-cinnamoyl coumarins using N,N'-(1,2-phenylene)bis(2-aminobenzamide) dichloro cobalt immobilized on mesoporous Al-SBA-15 as a new and recyclable catalyst

“…In addition, other significant properties of chalcones are monitoring cholesterol amount, blood purification, intensification of immune system, controlling blood pressure, improving metabolism, preventing of thrombus formation and suppressing acid secretion (53). Synthesis of coumarin-chalcone compounds is generally performed by Claisen-Schmidt aldol reaction between aromatic aldehydes and 3-acetylcoumarins using basic or acidic catalyst such as piperidine (54)(55)(56) and heterogeneous systems (e.g. Bi (OTf) 3 ) (57).…”

Molecular characterization of aldehydes and ketones in particle phase of mainstream and sidestream cigarette smoke

“…Commonly used derivatization reagents include hydroxylamine [26], 2,4-dinitrophenylhydrazine (DNPH) [27], Girard's reagent T [28–30], 2-hydrazino-1-methylpyridine (HMP) [31], cyclohexanedione [32], 4-[2-(trimethylammonio)ethoxy] benzen-aminium halide (4-APC) [33] and N,N-dicarboxymethyl hydrazine (DCMH) [34]. The Girard reagent is an old but very useful reagent for chemoselective derivatization of carbonyl compounds [30,35,36].…”