10264-31-0Relevant articles and documents
New observations on peptide bond formation using CDMT
Garrett, Christine E.,Jiang, Xinglong,Prasad, Kapa,Repi?, Oljan
, p. 4161 - 4165 (2002)
The optimized formation of the peptide bond by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) has been found to occur rapidly and essentially quantitatively in a one-pot, one-step procedure. This new method is effective for the coupling of a variety of reactive partners, including chiral amino acids (e.g. N-acetyl-L-leucine) without significant loss of configuration. Significant racemization was observed when the typical literature conditions were used, due to the formation of an azlactone intermediate which is configurationally unstable under the reaction conditions. A simpler, precipitative workup procedure is also disclosed in this report.
Development of chlorotriazine polymer dehydrocondensing reagents (Poly-Trzs)
Kunishima, Munetaka,Yamamoto, Kazuyoshi,Hioki, Kazuhito,Kondo, Tomohito,Hasegawa, Masumi,Tani, Shohei
, p. 2604 - 2612 (2007)
Polymer-type dehydrocondensing reagents comprising of a triazine dehydrocondensing reagent, itself in a polymerized form (Poly-Trz-MMs'), have been developed by exploiting the chemical properties of cyanuric chloride that readily binds to alcohol or amines. A chlorotriazine polymer bearing two alkoxy substituents at the 4- and 6- positions (Poly-O-Trz-Cl) was prepared by alternating copolymerization between cyanuric chloride and tetra(ethylene glycol). Similarly, polymers bearing both alkoxy and amino substituents (Poly-N-Trz-Cl) were synthesized from tetra(ethylene glycol) bis(4,6-dichlorotriazin-2-yl) ether 6 and tris(2-aminoethyl)amine 7 and/or ethylenediamine 8. All the polymers were shown to be good reagents for dehydrocondensation of carboxylic acids and amines in the presence of NMM, compared to the corresponding monomeric dehydrocondensing reagent (DMT-MM). The advantages of the polymeric reagents are as follows: (1) both the reaction and isolation procedure of dehydrocondensation can be greatly simplified, (2) the dehydrocondensation can be conducted in protic solvents as well as in common organic solvents, (3) the reagents can be efficiently prepared at a low cost, and (4) these reagents are considered eco-friendly, generating a lower amount of waste compared to conventionally related reagents because of high loading of the dehydrocondensing activity (ca. 3 mequiv/g).
Development of novel polymer-type dehydrocondensing reagents comprised of chlorotriazines
Kunishima, Munetaka,Yamamoto, Kazuyoshi,Watanabe, Yasunobu,Hioki, Kazuhito,Tani, Shohei
, p. 2698 - 2700 (2005)
A novel immobilized dehydrocondensing reagent comprised of a triazine-type dehydrocondensing reagent itself in a polymerized form was synthesized by copolymerization between tetra(ethylene glycol) bis(dichlorotriazinyl) ether and tris(2-aminoethyl)amine.
Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst
Singha, Krishnadipti,Ghosh, Subhash Chandra,Panda, Asit Baran
, p. 657 - 662 (2021)
Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.
Study of 1,3,5-triazine-based catalytic amide-forming reactions: Effect of solvents and basicity of reactants
Kunishima, Munetaka,Kitamura, Masanori,Tanaka, Hiroyuki,Nakakura, Ichiro,Moriya, Takahiro,Hiokib, Kazuhito
, p. 882 - 886 (2013)
Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6- dimethoxy-1,3,5-triazine (CDMT) was studied. The
Imido-substituted triazines as dehydrative condensing reagents for the chemoselective formation of amides in the presence of free hydroxy groups
Kitamura, Masanori,Sasaki, Suguru,Nishikawa, Riho,Yamada, Kohei,Kunishima, Munetaka
, p. 22482 - 22489 (2018)
In this paper, we discuss the synthesis of imido-substituted chlorotriazines and demonstrate their use in dehydrative condensation reactions. Chemoselective amide-forming reactions of amino alcohols using succinimido-substituted chlorotriazine (2A) proceeded smoothly. Occasionally, nonselectivity was problematic during the synthesis of hydroxy-substituted amides. Moreover, it was noteworthy that this method was applicable to hydroxy-substituted carboxylic acids that could have formed a lactone or an ester during the carboxylic acid activation step. The imido-substituted chlorotriazine (2A) was superior to the amido-substituted chlorotriazine and 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) in terms of reaction rates and yields.
Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- And 7-membered C-ring homologues
Kurouchi, Hiroaki
supporting information, p. 653 - 658 (2021/02/06)
A route to the direct amidation of aromatic-ring-tetheredN-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.
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.
