Scandium and Copper Triflate-Catalysed Acylaminoalkylation and Friedel-Crafts Alkylation Reactions

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

“…The formation of four condensed heterocyclic systems containing an isoindolobenzazepine fragment during the fusion of benzazepine and isoindole rings is theoretically possible: 6H-Isoindolo[2,1-a]benz-1-azepine (1), 7H-isoindolo[1,2-a]benz-2-azepine (2), 5H-isoindolo[2,1-b]benz-2-azepine (3), and 5H-isoindolo[1,2-b]benz-3-azepine (4). Of the heterocycles 1-4 only compound 4 has been studied sufficiently at the present time.…”

“…Of the heterocycles 1-4 only compound 4 has been studied sufficiently at the present time. Information on methods for the construction of and the chemical characteristics of the polycycles 1 and 2 can be gleaned from a limited number of publications [1][2][3][4]. We were only able to find mention of derivatives of isoindolo[2,1-b]benz-2-azepines 3 in nine papers [5][6][7][8][9][10][11][12][13], four of which are patents (10-13).…”

“…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].…”

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

“…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. 25 Working on Schiff bases 3a-c for a long time and biological interest of naphthoxazepines impelled us to synthesize different naphthoxazepines 7a-c in our laboratory.…”