71907-29-4Relevant academic research and scientific papers
C-H alkenylation of azoles with enols and esters by nickel catalysis
Meng, Lingkui,Kamada, Yuko,Muto, Kei,Yamaguchi, Junichiro,Itami, Kenichiro
, p. 10048 - 10051 (2013)
Rather u(Ni)que: Two new C-H alkenylation reactions, that is C-H/Ci￡O alkenylation and decarbonylative C-H alkenylation, of azoles are uniquely catalyzed by Ni/dcype. These azole alkenylation reactions are successfully applied to the convergent formal synthesis of siphonazoleB.
Synthesis and hplc-ecd study of cytostatic condensed o,n-heterocycles obtained from 3-aminoflavanones
Szappanos,Mándi, Attila,Gulácsi, Katalin,Lisztes, Erika,István Tóth, Balázs,Bíró, Tamás,Kónya-ábrahám, Anita,Kiss-Szikszai, Attila,Bényei, Attila,Antus, Sándor,Kurtán, Tibor
, p. 1 - 42 (2020/10/30)
Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3- aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and transaminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3- b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.
Method of coupling, and the coupling method using the aromatic group-substituted heterocyclic compound
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Paragraph 0292-0296; 0298-0299, (2020/09/17)
Provided is an easy method (coupling method) capable of easily synthesizing a compound group in which aromatic molecules and aromatic molecules are coupled, a compound group in which aromatic molecules and alkene molecules are coupled, and the like without producing halogen waste and without the need to use scarce and expensive palladium. A compound (A) shown by general formula (A): Ar-H and a compound (B1) shown by general formula (B1): RaOCO-Ar', a compound (B2) shown by general formula (B2): RbCH=C(Ar")2, or a compound (B3) shown by general formula (B3): RcOCOCH=C(Ar")2 are reacted in the presence of a nickel compound.
