Acyliminium ions derived from the rearrangement of Bischler-Napieralski cyclisation products

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review)

“…There have only been data on methods for the synthesis of isoindolo[1,2-a]benz-2-azepines in four publications [2][3][4]69].…”

“…During the action of scandium or copper triflate compound 86 undergoes cyclization to isoindolo[1,2-a]benz-2-azepine 87. Compound 85 can be converted into isoindolo[1,2-a]benz-2-azepine 87 in a single stage by the action of pyrophosphoryl chloride under more drastic conditions [3,4] Derivatives of benz-2-azepine can be used for the synthesis of isoindolo[1,2-a]benz-2-azepines [69]. When heated in methanol in the presence of 4-(dimethylamino)pyridine the benz-2-azepine 88 is converted into oxoisoindolo[1,2-a]benz-2-azepine 89.…”

A new and convenient synthetic method for 1,2,3,5,6,11b-hexahydroimidazo [1,2-d][1,4]benzoxazepine and its derivatives

“…1,[6][7][8] Alternatively, 2,3,4,5-tetrahydro-1,4-benzoxazepines are accessible by one of the following known benzoxazepine syntheses: (i) condensation of 2-aryloxyethylamines with 2-formylbenzoic acid to form aminonaphthalides followed by cyclization: (ii) rearrangement of methyl 2-(8-methoxy-2,3-dihydro-1,4-benzoxazepin-5-yl)benzoate using Bischler-Napieralski conditions; (iii) scandium or copper triflate-catalyzed acylaminoalkylation of α-methoxy-isoindolones with the formation of 1,4-benzoxazepines. [9][10][11] In 1981, Levan et al, 12,13 reported the isolation and characterization of unsubstituted 1,2,3,5,6,11b-hexahydroimidazo [1,2-d] [1,4]benzoxazepine in a tedious way without specifying…”

Synthesis of 2-aryl-1,2-dihydronaphtho[1,2-f][1,4]oxazepin-3(4H)-ones. Part I

“…7,8 It was found that dibenzo[b,f] [1,4]oxazepin-11(10H)-ones to be selective inhibitors of human immunodefiency virus (HIV) type 1 reverse transcriptase. 9 Known synthesis of benzoxazepines includes condensations of 2-aryloxyethylamines with 2-formylbenzoic acid, 10 rearrangement of methyl 2-(8-methoxy-2,3-dihydro-1,4-benzoxazepin-5-yl)benzoate using Bischler-Napieralski conditions 11 and scandium or copper triflate catalyzed acylaminoalkylation of α-methoxyisoindolones with the formation of 1,4-benzoxazepines in moderate yields. 12 Some oxazepines and benzoxazepines were synthesized from amides, [13][14][15] aminoacids, [16][17][18][19] esters, 20 acid chlorides, 21 flavones, 22,23 amines 24 and Mannich base.…”