82961-73-7Relevant academic research and scientific papers
Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions
Yuan, Yong,Li, Liang-Sen,Zhang, Lin,Wang, Feng,Jiang, Lin,Zuo, Lin,Wang, Qi,Hu, Jian-Guo,Lei, Aiwen
supporting information, p. 2768 - 2771 (2021/03/23)
An electrochemical oxidative cross-coupling reaction between 2.5-substituted-pyrazolin-5-ones and ammonium thiocyanate has been developed, which resulted in a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. It is worth noting that since the resulting cross-coupling products are nearly insoluble in MeCN, the pure product could be afforded without silica gel column purification. In addition, the prepared ammonium oxides are versatile building blocks for synthesizing functionalized pyrazole derivatives.
α-Fluorotricarbonyl Derivatives as Versatile Fluorinated Building Blocks: Synthesis of Fluoroacetophenone, Fluoroketo Ester and Fluoropyran-4-one Derivatives
Harsanyi, Antal,Lückener, Anne,Pasztor, Hedvig,Yilmaz, Zahide,Tam, Lawrence,Yufit, Dmitry S.,Sandford, Graham
supporting information, p. 3872 - 3878 (2020/06/09)
Fluorinated acyl-Meldrum's acid derivatives were synthesized by electrophilic fluorination of appropriate phenacyl Meldrum's acid substrates using Selectfluor. Reactions with water, ethanol, Grignard, and alkynyllithium reagents gave rise to the correspon
5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum's Acid Derivatives
Brosge, Felix,Kochs, Johannes Florian,Bregu, Mariela,Truong, Khai-Nghi,Rissanen, Kari,Bolm, Carsten
supporting information, p. 6667 - 6670 (2020/09/02)
At elevated temperatures, N-cyanosulfoximines react with Meldrum's acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and-cleaving processes.
Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones
Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.
supporting information, p. 197 - 200 (2018/12/13)
The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.
Chiral synthesis method for chiral beta-amino acid and synthesis method for medicinal intermediate
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Paragraph 0081; 0082; 0083; 0084, (2018/01/11)
The invention relates to a chiral synthesis method for chiral beta-amino acid. The chiral synthesis method comprises the following steps: reacting a compound shown in formula (II) with an acylation reagent to prepare anhydride intermediate reaction liquid under the action of alkali; adding Meldrum's acid into the anhydride intermediate reaction liquid, and performing reaction to generate a compound shown in formula (III); reacting the compound shown in formula (III) with a compound shown in formula (IV) to generate a compound shown in formula (V); reducing the compound shown in formula (V) to generate a compound shown in formula (VI); performing acidic hydrolysis on the compound shown in formula (VI) to generate a compound shown in formula (I), i.e., the chiral beta-amino acid. The chiral synthesis method has the advantages of convenience for synthesis, low cost and simple process, and compared with a disclosed preparation method, is more suitable for industrial production.
Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: When ketoamides surpass ketoesters
Du, Haiying,Rodriguez, Jean,Bugaut, Xavier,Constantieux, Thierry
supporting information, p. 8458 - 8466 (2014/07/08)
Our findings on the bifunctional squaramide-catalyzed enantioselective conjugate addition of ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene ketoamides, unlike the extensively studied ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted to rationalize the observed reactivity and selectivity. The high level of diastereocontrol, along with the amenability of the amide group to postfunctionalization, dramatically increase the synthetic usefulness of the transformation.
Asymmetric total synthesis of the indole alkaloid cyclopiazonic acid and first structure-activity data
Beyer, W.R. Christian,Woithe, Katharina,Lüke, Bettina,Schindler, Michael,Antonicek, Horst,Scherkenbeck, Jürgen
experimental part, p. 3062 - 3070 (2011/05/17)
The indole alkaloid α-cyclopiazonic acid (CPA) is one of the few known inhibitors of sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) besides the terpenoids thapsigargin and artemisinin. We report here the first asymmetric total synthesis of cy
A facile synthesis of pyrimidin-4-ones
Guo, Cheng
scheme or table, p. 548 - 549 (2010/10/02)
A facile synthesis of 2,6-disubstituted pyrimidin-4-ones and 2,5,6-trisubstituted pyrimidin-4-ones from commercially available materials with application of microwave technology in key steps is described.
Microwave synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas Aeruginosa
Oliver, Colin M.,Schaefer, Amy L.,Greenberg, E. Peter,Sufrin, Janice R.
experimental part, p. 1559 - 1575 (2010/02/16)
The bacterial quorum sensing (QS) signal molecule 3-oxo-dodecanoyl-L- homoserine lactone (OdDHL) is produced by the opportunistic pathogen Pseudomonas aeruginosa and controls expression of virulence factors associated with life threatening infections in i
A novel route to 5-substituted 3-isoxazolols. Cyclization of N,O-diBoc β-keto hydroxamic acids synthesized via acyl Meldrum's acids
Sorensen, Ulrik S.,Falch, Erik,Krogsgaard-Larsen, Povl
, p. 1003 - 1007 (2007/10/03)
3-Isoxazolols are most often synthesized from a β-keto ester and hydroxylamine. This cyclization typically gives rise to a major byproduct, the corresponding 5-isoxazolone. We have found that N,O-diBoc-protected β- keto hydroxamic acids can be synthesized and cyclized to 5-substituted 3- isoxazolols without formation of any byproduct. We present a novel and versatile three-step procedure in which carboxylic acid derivatives are converted into acyl Meldrum's acids which, upon aminolysis with N,O-bis(tert- butoxycarbonyl)hydroxylamine, lead to the N,O-diBoc-protected β-keto hydroxamic acids. These hydroxamic acid analogues were then, upon treatment with hydrochloric acid, cyclized to the corresponding 5-substituted 3- isoxazolols.
