Synthesis of a family of 3-alkyl- or 3-aryl-substituted 1,2-dihydroquinazolinium salts and their isomerization to 4-iminium-1,2,3,4-tetrahydroquinolines |
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Authors: | Vicente José Chicote María Teresa Martínez-Martínez Antonio Jesús Bautista Delia Jones Peter G |
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Institution: | Grupo de Química Organometálica, Departamento de Química Inorgánica, Universidad de Murcia, Apartado 4021, 30071, Murcia, Spain. jvs1@um.es |
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Abstract: | A straightforward synthesis of substituted 1,2-dihydroquinazolinium triflates (3) is reported by reaction of 2-imino-substituted anilines with a range of carbonyl compounds in the presence of triflic acid via intermediate iminium salts. Similar reactions with di- or trialdehydes and triflic acid give bis- or tris-(1,2-dihydroquinazolinium) salts. Some 4-methyl substituted 1,2-dihydroquinazolinium salts rearrange, under various conditions, to their corresponding 4-iminium-1,2,3,4-tetrahydroquinolinium isomers (7). Most of salts 3 derived from ketones are rather unstable, which prevents their isolation or full characterization. The crystal structures of various 3 and 7 salts have been determined. |
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