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Communication | Regular issue | Vol 16, No. 10, 1981, pp.1693-1696
Published online, 1st January, 1970
DOI: 10.3987/R-1981-10-1693
Synthesis of 3,4-Dihydroquinazolines via Cyclic N-Diazonium Ions

Richard Kreher* and Udo Bergmann

*Institut für Chemie, Medizinische Hochschule Lübeck, Ratzeburger Allee 160, D-2400, Germany


The condensation of 2-azidomethylanilines with aromatic aldehydes leads to tne formation of the corresponding azomethines. Treatment with tetrafluoroboric acid results in the generation of phenylogous azidomethyl-iminium salts giving rise to the formation of 2-aryl-3,4-dihydroquinazolines. Cyclic N-diazonium ions are involved as reactive intermediates and synthetic precursors for the annelation of the 6-membered nitrogen heterocycle.