35304-85-9Relevant academic research and scientific papers
Iodine(III)-Mediated Contraction of 3,4-Dihydropyranones: Access to Polysubstituted γ-Butyrolactones
Dagenais, Robin,Lussier, Tommy,Legault, Claude Y.
supporting information, p. 5290 - 5294 (2019/09/03)
Functionalized γ-butyrolactones are privileged structures in the field of medicinal chemistry; they are found in numerous natural products and synthetic compounds with diverse biological activities. The oxidative ring contraction of 3,4-dihydropyran-2-one derivatives represents a promising yet underappreciated strategy to access these compounds. To the best of our knowledge, very few examples of this strategy have been reported, with limited investigation of the influence of stereogenic centers on the starting dihydropyranones. We investigated the iodine(III)-mediated contraction of a representative set of dihydropyranone derivatives. The method gives rapid access to functionalized γ-butyrolactones in good yields. The reaction scope was investigated, and the method was found to support various levels of substituents, even enabling access to sterically congested quaternary centers. The stereoselectivity was investigated using chiral substrates and a chiral iodine(III) reagent.
Preparation of α-Acyloxy Ketones via Visible-Light-Driven Aerobic Oxo-Acyloxylation of Olefins with Carboxylic Acids
Zhang, Qing-Bao,Ban, Yong-Liang,Zhou, Da-Gang,Zhou, Pan-Pan,Wu, Li-Zhu,Liu, Qiang
supporting information, p. 5256 - 5259 (2016/11/02)
We developed a visible-light driven oxo-acyloxylation of aryl alkenes with carboxylic acids and molecular oxygen. A metal-free photoredox system, consisting of an acridinium photocatalyst, an organic base, and molecular sieve (MS) 4 ?, promotes chemoselective aerobic photooxidation of aryl alkenes. This approach may provide a green, practical, and metal-free protocol for a wide range of α-acyloxy ketones.
Visible-Light-Promoted Metal-Free Aerobic Oxidation of Primary Amines to Acids and Lactones
Cheng, Xiaokai,Yang, Bo,Hu, Xingen,Xu, Qing,Lu, Zhan
supporting information, p. 17566 - 17570 (2016/11/29)
A unique metal-free aerobic oxidation of primary amines via visible light photocatalytic double carbon–carbon bonds cleavage and multi carbon–hydrogen bonds oxidation was observed. Aerobic oxidation of primary amines could be controlled to afford acids by using dioxane with 18 W CFL, and lactones by using DMF with 8 W green LEDs, respectively. A plausible mechanism was proposed based on control experiments. This observation showed direct evidences for the fragmentation in the aerobic oxidation of aliphatic primary amines.
Facile aerobic photooxidative oxylactonization of oxocarboxylic acids in fluorous solvents
Tada, Norihiro,Cui, Lei,Ishigami, Takafumi,Ban, Kazunori,Miura, Tsuyoshi,Uno, Bunji,Itoh, Akichika
, p. 3007 - 3009,3 (2020/09/16)
We developed efficient aerobic photooxidative oxylactonizations of oxocarboxylic acids promoted by trifluoroacetic anhydride with molecular oxygen as the terminal oxidant in the fluorous solvent FC-72.
Intramolecular PIFA-mediated alkyne amidation and carboxylation reaction
Tellitu, Imanol,Serna, Sonia,Herrero, M. Teresa,Moreno, Isabel,Dominguez, Esther,SanMartin, Raul
, p. 1526 - 1529 (2007/10/03)
(Chemical Equation Presented) The hypervalent iodine reagent PIFA promotes the intramolecular electrophilic cyclization of easily accessible alkynylamides and alkynyl carboxylic acids, leading to the formation of pyrrolidinone and lactone skeletons, respe
THERAPEUTIC AGENT FOR DIABETES
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, (2008/06/13)
A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4and R5are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6is a hydrogen atom or an amino-protecting group; R1is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.
