10283-70-2Relevant articles and documents
Acyl iodides in organic synthesis: XI. Unusual N-C bond cleavage in tertiary amines
Voronkov,Tsyrendorzhieva,Rakhlin
, p. 481 - 484 (2008)
Acyl iodides reacted with excess primary and secondary amines in a way similar to acyl chlorides, yielding the corresponding carboxylic acid amide and initial amine hydroiodide. Reactions of tertiary amines with acyl iodides were accompanied by cleavage of the N-C bond with formation of the corresponding N,N-di(hydrocarbyl)carboxamide and alkyl iodide. In the presence of excess tertiary amine the latter was converted into quaternary tetra(hydrocarbyl) ammonium iodide.
Oxidative amidation of benzyl alcohol, benzaldhyde, benzoic acid styrene and phenyl acetylene catalyzed by ordered mesoporous HKUST-1-Cu: Effect of surface area on oxidative amidation reaction
Mohebali, Haleh,Mahjoub, Ali Reza,Karimi, Meghdad,Heydari, Akbar
, (2019)
HKUST-1-Cu synthesized in the presence and absence of P-123 trough solvotermal method. After characterization using some different microscopic and spectroscopic techniques such as XRD, FT-IR, SEM, ICP, BET and TEM its catalytic activity was investigated in the oxidative coupling of benzyl alcohol, benzaldhyde, benzoic acid, styrene and phenyl acetylene with N,N-dialkylformamides for the preparation of N,N-dimethylformamides. Different derivatives of tertiary amides were synthesized in moderate to good yields in the presence of just ~0.28?mol% of this catalytic system. Reusability of the synthesized catalysts was examined and catalysts were reusable for 8 times without significant decrease in optimized conditions.
A medium fluorous Grubbs-Hoveyda 2nd generation catalyst for phase transfer catalysis of ring closing metathesis reactions
Kobayashi, Yuki,Inukai, Sae,Kondo, Natsuki,Watanabe, Tomoko,Sugiyama, Yuya,Hamamoto, Hiromi,Shioiri, Takayuki,Matsugi, Masato
, p. 1363 - 1366 (2015)
A fluorous Grubbs-Hoveyda metathesis catalyst supported on Teflon powder, that readily moves between the solid phase (Teflon) and the liquid phase (DMF) was prepared. By modulating the hydrophobicity of the reaction medium at the end of the reaction, the supported catalyst could be recovered by simple filtration even though the catalyst existed in a homogeneous state during the reaction. In RCM reactions, the catalyst could be reused up to three times with only a slight loss in reactivity with each subsequent cycle.
Oxidative amidation of aromatic aldehydes with amine hydrochloride salts catalyzed by silica-coated magnetic carbon nanotubes (MagCNTs@SiO 2)-immobilized imine-Cu(I)
Saberi, Dariush,Heydari, Akbar
, p. 101 - 108 (2014)
Mesoporous silica-coated magnetic carbon nanotubes were prepared; their surface functionalization, followed by reaction with CuI, were carried out to develop a Cu-grafted functionalized mesoporous material. This system is able to catalyze oxidative amidation of aromatic aldehydes with amine hydrochloride salts, generating amide derivatives in moderate to good yields. Magnetic properties of this catalyst led to easy separation as well as providing significant recyclability.
Metal-Free Transamidation of Secondary Amides by N-C Cleavage
Rahman, Md. Mahbubur,Li, Guangchen,Szostak, Michal
, p. 12091 - 12100 (2019/10/11)
Transamidation reactions represent a fundamental chemical process involving conversion of one amide functional group into another. Herein, we report a facile, highly chemoselective method for transamidation of N-tert-butoxycarbonylation (N-Boc) activated secondary amides that proceeds under exceedingly mild conditions in the absence of any additives. Because this reaction is performed in the absence of metals, oxidants, or reductants, the reaction tolerates a large number of useful functionalities. The reaction is compatible with diverse amides and nucleophilic amines, affording the transamidation products in excellent yields through direct nucleophilic addition to the amide bond. The utility of this methodology is highlighted in the synthesis of Tigan, a commercial antiemetic, directly from the amide bond. We expect that this new metal-free transamidation will have broad implications for the development of new transformations involving direct nucleophilic addition to the amide bond as a key step.
Synthesis of Amides from Alcohols and Amines Through a Domino Oxidative Amidation and Telescoped Transamidation Process
Drageset, Audun,Bj?rsvik, Hans-René
, p. 4436 - 4445 (2018/09/11)
The amide bond formation is of paramount importance in organic synthesis, both within academic research and industrial development and manufacturing of pharmaceutical chemicals and other biologically active compounds. Despite this fact, as well as the ever-increasing treatment costs of side streams and other environmental concerns regarding handling and transportation of hazardous reagents, contemporary synthesis has elicited few new reactions and methods for the preparation of amides. Herein, we reveal a high yielding and expedite two-step telescoped synthetic process that comprises a domino oxidative amidation and transamidation for the creation of amides. The process utilizes alcohols and amines as reaction pairs with TEMPO and Fe ions as catalytic system and 1,3-dichloro-5,5-dimethyl hydantoin as a terminal oxidant. The oxidative amidation and transamidation process is conducted under benign reaction conditions and short reaction time (≈ 30 min.) in a two-step telescoped fashion by means of a multi-jet oscillating disk (MJOD) continuous-flow reactor platform. The disclosed process integrates alcohol oxidation and amide formation to afford target amide in yields up to 90 %. The method operates with both primary and secondary amines together, but was hampered when bulky amines and/or alcohols were used as reagent/substrate.
