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2004
Imidazole derivatives
R 0190
Regio- and Stereospecific Syntheses of syn- and anti-1,2-Imidazolylpropylamines
the Reaction of 1,1'-Carbonyldiimidazole with syn- and anti-1,2-Amino
47- 116 from
Alcohols. — Thermal treatment of the anti-amino alcohols (I) and (VI) with CDI (II)
leads to anti-1,2-imidazolylpropylamines. Starting from syn-amino alcohols the
syn-products are obtained. This proceeds via initial formation of imidazolylcarbamates
as indicated by isolation of the carbamate (X) from the amino alcohol (VIII) at 25 °C.
These carbamates can undergo displacement of the carbonyl group supported by the
neighboring tertiary amino group leading to aziridinium intermediates. The latter react
regio- and stereospecifically with the imidazolide. — (MULVIHILL*, M. J.;
CESARIO, C.; SMITH, V.; BECK, P.; NIGRO, A.; J. Org. Chem. 69 (2004) 15,
5124-5127; OSI Pharm. Inc., Farmingdale, NY 11735, USA; Eng.) — Jannicke
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