1207-96-1Relevant academic research and scientific papers
Facile synthesis of acridines via Pd(0)-diphosphine complex-catalyzed tandem coupling/cyclization protocol
Wang, Ting-Jun,Chen, Wen-Wen,Li, Yi,Xu, Ming-Hua
, p. 6580 - 6586 (2015/06/16)
A facile and efficient approach for the synthesis of a variety of acridines via the tandem coupling/cyclization of substituted 2-bromobenzaldehydes and anilines is described. The reaction can be accomplished with ease in the presence of a catalytic amount of Pd2(dba)3 and diphosphine ligand dppf, providing a broad range of substituted acridines in good to excellent yields (up to 99%). The Lewis acid, AlCl3, is required to promote the cyclization for less electron-rich anilines.
Diels-Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives
Consonni, Roberto,Dalla Croce, Piero,Ferraccioli, Raffaella,La Rosa, Concetta
, p. 1809 - 1814 (2007/10/03)
N-Tosyl- and N-alkylidene-sulfonyl substituted 1,4-dihydro-2A-3,1-benzoxazin-2-ones 2c-g easily undergo thermal carbon dioxide extrusion leading to the aza-ortho-xylylenes 3c-g. The intermediates 3c,d can be trapped by electron-poor ethylenic and acetylenic dienophiles, giving tetrahydroquinoline and quinoline derivatives. The reactions of 2c with non-symmetrical dienophiles are completely regioselective. N-Alkylidenesulfonyl substituted aza-orthro-xylylenes 3f-g undergo intramolecular Diels-Alder reactions leading to the tricyclic compounds 10 and 11, while the aza-ortho-xylylene generated from 4-(hex-5-enyl)-N-(4-methylphenylsulfonyl)-1,4-tetrahydro-2H-3,1-benzoxazin-2-one undergoes a [1,5] hydrogen shift leading to N-[2-(1E)-hepta-1,6-dien-1-ylphenyl]-4-methylbenzenesulfonamide.
