145291-94-7Relevant academic research and scientific papers
Metal-Free, DBU-Mediated, Microwave-Assisted Synthesis of Benzo[c]xanthones by Tandem Reactions of Alkynyl-1,3-diketones
Liang, Yi-En,D. Barve, Balaji,Kuo, Yao-Haur,Fang, Hsu-Wei,Kuo, Ting-Shen,Li, Wen-Tai
supporting information, p. 505 - 511 (2020/12/01)
A base-mediated, green, microwave-assisted efficient preparation of a diverse benzoxanthone library from variety of readily accessible γ-alkynyl 1,3-diketones is reported. The synthesis is based on tandem reactions involving intramolecular cyclization, propargyl-allenyl isomerization, and electrocyclization in one pot. Some of the benzoxanthones are also synthesized by the one-pot reaction of 1,3-diketone and alkynyl bromide under basic heating conditions. This transformation also results in the construction of one new C?C bond and one new C?O bond. (Figure presented.).
Solid state aggregation of cyclic iodonium ylides
Li, Guobi,Rheingold, Arnold L.,Protasiewicz, John D.
supporting information, (2022/01/28)
Iodonium ylides (ArI=CR(R")) represent unusual hypervalent iodine(III) sources of carbene equivalents. While their reactivity is well-described, their detailed structural chemistry is somewhat limited due to their thermal instability. Cyclic iodonium ylides typically have greater thermal stability than acyclic ylides, but so far few such materials have been examined by single crystal X-ray diffraction methods. This report details the synthesis of two cyclic iodonium ylides and their association in the solid state by intermolecular I???O interactions.
Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives
Zhang, Ying,Chen, Jing-Lei,Chen, Zhen-Bang,Zhu, Yong-Ming,Ji, Shun-Jun
, p. 10643 - 10650 (2015/11/18)
An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.
Synthesis and characterization of binary-complex models of ureas and 1,3-dicarbonyl compounds: Deeper insights into reaction mechanisms using snap-shot structural analysis
Azuma, Takumi,Kobayashi, Yusuke,Sakata, Ken,Sasamori, Takahiro,Tokitoh, Norihiro,Takemoto, Yoshiji
, p. 1805 - 1817 (2014/03/21)
The mechanism of the enantioselective Mannich reaction catalyzed by a hydrogen-bond (HB)-donor bifunctional organocatalyst has been fully investigated using experimental evidence and computational analysis. Several binary complexes have been designed as models of a catalyst and a nucleophile, where the urea moieties were linked to a 1,3-dicarbonyl compound through the diphenylacetylene motif. X-ray analysis of models 9 and 10 showed that the two N-H protons of the ureas interacted with the same carbonyl group via a double HB interaction. Further investigation of the crystallographic structure of 11 allowed for the direct observation of the labile ammonium-enolate intermediate formed between a bifunctional amino urea and 1,3-diketone. The β-keto ester-amino urea complex 12 reacted with several electrophiles at a remarkably fast rate to provide the corresponding adducts 15 and 17 as single diastereomers in excellent yields, respectively. A density functional theory calculation disclosed the details of the deprotonation and C-C bond-forming steps of the enantioselective Mannich reaction. The deprotonation of the 1,3-dicarbonyl moiety occurred predominantly via the enol form to give the ammonium - enolate intermediate. These results should provide a deeper and more accurate understanding of the functional roles of the HB-donor and Bronsted base moieties of the catalyst.
Synthesis of Cyclic Iodonium Ylides - 3H-1λ3-Benziodiol-1-ylium Ylides via Transylidation of Iodonium Ylides to Iodides
Yang, Rui-Yang,Dai, Li-Xin,Chen, Cheng-Gang
, p. 1487 - 1488 (2007/10/02)
Cyclic iodonium ylides are synthesised via an unprecedented transylidation of iodonium ylide to aryl iodides; the structure of one cyclic iodonium ylide is determined by X-ray crystallography.
