The synthesis of fused ring nitrogen heterocycles via regiospecific intramolecular heck reactions

Application of a catalytic palladium biaryl synthesis reaction, via C–H functionalization, to the total synthesis of Amaryllidaceae alkaloids

“…8 Grigg and co-workers favoured the investigation of catalytic methods and observed that the Heck reaction 9 of N-(2-iodobenzoyl)-indole, and the 3-methylindole derivative, resulted in cyclization at C-2 of the indole nucleus when they used 10 mol% Pd(OAc) 2 and 20 mol% PPh 3 , in the presence of K 2 CO 3 and Et 4 NCl, in refluxing acetonitrile. 10 Other investigations have also revealed the preference for cyclization at C-2 when the halogen was bonded to the N-benzoyl or N-benzyl fragment of the indole substrate. 11 Harayama and co-workers have recently investigated the palladium catalyzed cyclizations of N-2-halobenzylindolines.…”

Isoindoloindolones - biological activities and syntheses

“…[11][12][13][14][15][16][17][18] It was first explored by Itahara in 1979 [11][12][13][14] and was further developed by many other research groups. 15 Electron rich tethered arenes gave better yields than unsubstituted arenes.…”

Synthesis of 8-oxoprotoberberines using acid-mediated cyclization or the Heck reaction

“…1) constitute an important class of natural products that are typically characterized by a tetracyclic ring skeleton with an isoquinoline core [1,2]. Due to their diverse biological properties, such as antitumor, antiviral, and antimicrobial activities [3][4][5][6][7][8][9][10][11], considerable attention has been focused on the efficient synthesis of these alkaloids [12][13][14][15][16][17][18][19][20][21]. However, previously reported methods require the use of harsh conditions [13,14], involve lengthy sequences with low overall yields [18], need complicated starting materials [18,19,21], and various substituted protoberberine derivatives are in short supply [12][13][14].…”