330467-78-2Relevant academic research and scientific papers
A further decrease in the catalyst loading for the palladium-catalyzed direct intramolecular arylation of amides and sulfonamides
Conde, Nerea,Churruca, Fátima,Sanmartin, Raul,Herrero, María Teresa,Domínguez, Esther
, p. 1525 - 1531 (2015/05/26)
The direct arylation of N-substituted o-bromobenzanilides and benzenesulfonamides via C-H bond functionalization has been developed using very low catalyst loadings. This novel cost-effective and more sustainable method relies on a PCN-type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic systems. The beneficial effect of water as cosolvent has been observed in this process, which is not seriously influenced by electronic effects at the arene moieties or sterically demanding substituents at the amide or sulfonamide nitrogen. In addition, a number of experiments (kinetic plot, poisoning assays, TEM, ESI) have been performed in order to understand the role of the employed palladium complex in this reaction.
Intramolecular direct dehydrohalide coupling promoted by KOtBu: Total synthesis of amaryllidaceae alkaloids anhydrolycorinone and oxoassoanine
De, Subhadip,Ghosh, Santanu,Bhunia, Subhajit,Sheikh, Javeed Ahmad,Bisai, Alakesh
, p. 4466 - 4469 (2012/10/29)
A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works only in the presence of potassium tert-butoxide.
Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline
Miyata, Okiko,Shirai, Atsushi,Yoshino, Shintaro,Nakabayashi, Toshiki,Takeda, Yoshifumi,Kiguchi, Toshiko,Fukumoto, Daisuke,Ueda, Masafumi,Naito, Takeaki
, p. 10092 - 10117 (2008/02/13)
Radical addition-cyclization-elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu3SnNMe2, Bu3SnD, and/or D2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.
