2904-62-3Relevant articles and documents
Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
Pan, Ting,Gao, Xing,Yang, Sen,Wang, Lan,Hu, Yimin,Liu, Min,Wang, Wei,Wu, Yongjun,Zheng, Bing,Guo, Hongchao
, p. 5750 - 5754 (2021/08/16)
In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).
An isomerization-1,3-dipolar cycloaddition tandem reaction towards the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines from O-allyl compounds
Krompiec, Stanis?aw,Bujak, Piotr,Malarz, Joanna,Krompiec, Micha?,Skórka, ?ukasz,Pluta, Tadeusz,Danikiewicz, Witold,Kania, Magdalena,Kusz, Joachim
experimental part, p. 6018 - 6031 (2012/09/22)
A new strategy for the synthesis of 3-aryl-4-methyl-5-O-substituted isoxazolines via tandem catalytic isomerization of O-allyl systems to O-(1-propenyl) systems-1,3-dipolar cycloaddition (1,3-DC) to nitrile oxides is presented. The influence of the heteroatom in Ph-X-CH=CHCH3 (X=O, S, or Se) on the regio- and stereoselectivity of ArCNO 1,3-cycloaddition to these dipolarophiles is analyzed as well. The dipolarophiles were obtained via [RuClH(CO)(PPh3)3]-, [RuH2(CO)(PPh 3)]- or base (KOH/18-crown-6)-catalyzed double bond migration in corresponding allyl ethers, O-allyl acetals, PhS- and PhSe-allyl systems. Cycloadditions of nitrile oxides to O-(1-propenyl) systems were fully regioselective whereas in the reactions of ArCNO with the PhS-(1-propenyl) and PhSe-(1-propenyl) systems both possible regioisomers were formed. It was established that within the majority of dipolarophiles of ROCHCHCH3 type 1,3-DC is concerted, while for some dipolarophiles of RXCH=CHCH3 (X=O and R=Ph3C, 2,3-dihydroxypropyl, tetrahydropyran-2-yl; X=S or Se and R=Ph) type 1,3-DC turns into a two-step reaction with simultaneous rotation about C-C bond. The results of the experiments have been analyzed theoretically using DFT calculations. The results of these calculations agreed well with the experimental data.
Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents
Reddy, Doma Mahendhar,Qazi, Naveed A.,Sawant, Sanghpal D.,Bandey, Abid H.,Srinivas, Jada,Shankar, Mannepalli,Singh, Shashank K.,Verma, Monika,Chashoo, Gousia,Saxena, Arpita,Mondhe, Dilip,Saxena, Ajit K.,Sethi,Taneja, Subhash C.,Qazi, Gulam N.,Sampath Kumar
body text, p. 3210 - 3217 (2011/07/31)
Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ring (α-methylene- γ-butyrolactone). Majority of the compounds exhibited improved anti-cancer activity compared to the parthenin, when screened for their in vitro cytotoxicity against three human cancer cell lines viz., SW-620, DU-145 and PC-3. In vivo screening of select analog revealed improved anti-cancer activity with low mammalian toxicity as compared to parthenin. The results of the cytotoxicity pattern of these derivatives reveals the SAR of these sesquiterpinoid lactones and possible role of α,β-unsaturated ketone of parthenin in inhibiting NF-kB. A mechanistic correlation of anti-cancer activity along with in vivo and western blotting experiments has been described.