Atom-Economical Synthesis of 2-Aminoimidazoles via [3+2] Annulation Catalyzed by Titanacarborane Monoamide

Yang Wang, Hao Shen, Zuowei Xie*

*Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, P. R. of China, Email: zxiecuhk.edu.hk

Y. Wang, H. Shen, Z. Xie, Synlett, 2011, 969-973.

DOI: 10.1055/s-0030-1259713

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Abstract

Reactions of propargylamines with carbodiimides, in the presence of 5 mol% of the titanacarborane monoamide [σ:η¹:η⁵-(OCH₂)(Me₂NCH₂)C₂B₉H₉]Ti(NMe₂), afford a new class of substituted 2-aminoimidazoles via [3+2] annulation in good to excellent yields. A possible reaction mechanism is proposed.

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Key Words

catalysis, heterocycles, hydroamination, imidazoles, metallacarborane

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ID: J60-Y2011-1030