56776-81-9Relevant academic research and scientific papers
New alkyne esters and alkyneamide plant antibacterial agents
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Paragraph 0059-0062; 0063, (2022/03/02)
The present invention relates to a class of propyne esters and propyneamide compounds and synthetic methods thereof, and drugs containing the compound and applications thereof. The two types of compounds have efficient and broad-spectrum inhibitory activity for more than ten kinds of plant pathogenic fungi, and at the same time have the characteristics of simple structure, easy large-scale preparation and high safety of animals and plants, and can be used as active ingredients for the development of new plant antibacterial agents with high efficiency and low toxicity.
Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages
Wang, Shi-Meng,Zhao, Chuang,Zhang, Xu,Qin, Hua-Li
, p. 4087 - 4101 (2019/04/30)
The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.
Boronic acid-DMAPO cooperative catalysis for dehydrative condensation between carboxylic acids and amines
Ishihara, Kazuaki,Lu, Yanhui
, p. 1276 - 1280 (2016/02/05)
Arylboronic acid and 4-(N,N-dimethylamino)pyridine N-oxide (DMAPO) cooperatively catalyse the dehydrative condensation reaction between carboxylic acids and amines to give the corresponding amides under azeotropic reflux conditions. This cooperative use is much more effective than their individual use as catalysts, and chemoselectively promotes the amide condensation of (poly)conjugated carboxylic acids. The present method is practical and scalable, and has been applied to the synthesis of sitagliptin and a drug candidate.
Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 6582 - 6586 (2015/06/02)
The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides
Koo, Jaeyoung,Park, Hyun-Sub,Shin, Seunghoon
supporting information, p. 834 - 839 (2013/02/25)
Silver-catalyzed cycloisomerizations of 1,6-enynes derived from propiolamides led to a selective formation of Alder-ene type 1,4-dienes. Interestingly, AgNTf2 outperformed gold or platinum catalysts in terms of selectivity and reactivity, providing the 1,4-dienes at room temperature. The presence of C(5) carbonyl group in combination with Ag salts is key to the selectivity and the β-oxo coordinated silver carbenoids were proposed as an intermediate based on the reaction profiles.
FORMAL 1,6-INSERTION OF AN ALKYLIDENECARBENE INTO A CARBON-HYDROGEN BOND. UNVEILING OF A STEPWISE REACTION MECHANISM.
Gilbert, John C.,Blackburn, Brent K.
, p. 4727 - 4730 (2007/10/02)
The formation of 1,3-dimethylquinol-2-one (6a) by reaction of N-methyl-N-phenyl-2-oxopropanamide (1a) with diethyl(diazomethyl)phosphonate (2), an apparent C-H insertion by an alkylidenecarbene, is shown to involve a stepwise rather than a concerted reaction pathway.
