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2005
Imidazole derivatives
R 0190
The Reaction of Carbonyldiimidazole with Alcohols to Form Carbamates and
— A recently reported synthesis of N-alkylimidazoles from alco11- 140 N-Alkylimidazoles.
hols and carbonyldiimidazole is reinvestigated. The study reveals that aliphatic alcohols such as (I) and (IV) do not give the expected N-alkylimidazoles under the reported
mild reaction conditions and even at prolonged heating in NMP. The carbamates (III)
and (V) are isolated as the sole products. Benzylic alcohols such as (VI) give the corresponding carbamates at room temperature whereas in NMP at 170 °C decarboxylation produces alkylimidazoles (VII). Benzhydrol (VIII) shows similar reaction results.
— (TANG, Y.; DONG, Y.; VENNERSTROM*, J. L.; Synthesis 2004, 15, 2540-2544;
Coll. Pharm., Univ. Nebr. Med. Cent., Omaha, NE 68198, USA; Eng.) — Mais
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