333349-63-6Relevant academic research and scientific papers
Palladium-assisted biaryl coupling reaction of 1-(2-iodobenzoyl)-1,2,3,4-tetrahydroquinoline
Harayama, Takashi,Sato, Tomonori,Hori, Akihiro,Abe, Hitoshi,Takeuchi, Yasuo
, p. 527 - 530 (2005)
The biaryl coupling reaction of 1-(2-iodobenzoyl)-1,2,3,4-tetrahydroquinoline using Pd reagent was examined. The reaction proceeded smoothly to produce, 5,6-dihydro-4H,8H-pyrido[3,2,1-de]phenanthridin-8-one in excellent yield.
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.
