12 research outputs found

    DIAZAFULVENONES - THERMAL ISOMERIZATIONS AND ELIMINATIONS IN ALKOXYCARBONYL AND ANILINOCARBONYL DERIVATIVES OF IMIDAZOLE

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    4-Carbonyl-4H-imidazole (10) and 2-carbonyl-2H-imidazole (11) are formed by flash vacuum pyrolysis of methyl 4- and 2-imidazolecarboxylates, respectively. 10 and 11 dimerize to diketopiperazines 14 and 16, respectively. The same products are also obtained from 4- and 2-(anilinocarbonyl)imidazoles, respectively. Methyl imidazole-1-carboxylate (4) on pyrolysis gives a ca. 1:1 mixture of the same ketenes 10 and 11, which dimerizes to a 1:2:1 ratio of diketopiperazines 14–16. In contrast, ethyl imidazole-1-carboxylate gave CO, ethylene, and imidazole as the major products. The pyrolysis reactions were monitored by low-temperature infrared and high-temperature mass spectrometry
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