180747-56-2Relevant articles and documents
N-acyltriazinedione; a novel acylating reagent synthesized from a triazinone-type condensing reagent
Yamada, Kohei,Lee, Jeongsu,Kota, Mika,Karuo, Yukiko,Kitamura, Masanori,Kunishima, Munetaka
, p. 498 - 502 (2021/05/27)
In this paper, we report the synthesis of N-acyltriazinedione via the unexpected O–N acyl rearrangement of acyloxytriazinone and its utility as an acylating reagent. N-Acyltriazinedione can be isolated by silica gel column chromatography and reacts with amines in the absence of any base to give the corresponding amides in good yields.
Development of Triazinone-Based Condensing Reagents for Amide Formation
Yamada, Kohei,Kota, Mika,Takahashi, Kensuke,Fujita, Hikaru,Kitamura, Masanori,Kunishima, Munetaka
, p. 15042 - 15051 (2019/11/19)
Novel triazinone-based condensing reagents have been developed. The palladium-catalyzed O-N allylic rearrangement of 2-(allyloxy)-4,6-dichloro-1,3,5-triazine and subsequent regioselective substitution using alcohols and an amine afforded chlorotriazinones, which can be readily converted using N-methylmorpholine into the corresponding condensing reagents. The condensation of carboxylic acids and amines using these reagents proceeded to afford the desired amides in good yields. In comparison with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, the newly synthesized triazinone-based condensing reagents exhibited higher reactivity.
A comparative study of amide-bond forming reagents in aqueous media – Substrate scope and reagent compatibility
Badland, Matthew,Crook, Robert,Delayre, Bastien,Fussell, Steven J.,Gladwell, Iain,Hawksworth, Michael,Howard, Roger M.,Walton, Robert,Weisenburger, Gerald A.
supporting information, p. 4391 - 4394 (2017/10/20)
A survey of amidation reagents demonstrating DIC-HOPO, DMT-MM, COMU-collidine, TPTU-NMI, EEDQ, CDI and EDC-Oxyma to be effective for the coupling of carboxylic acids with amines in the presence of water and the absence of problematic dipolar aprotic solvents is reported. DMT-MM was shown to provide the best yields for the coupling of a secondary amine, TPTU-NMI and COMU-collidine for aniline, whilst the combination of DIC with HOPO afforded the broadest substrate scope and the highest yields for a sterically demanding carboxylic acid.
