Volume 19, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Cobalt-Mediated (2 + 2 + 2) Cycloadditions of Alkynes to the Imidazole 4,5 Double Bond. First Synthesis of the 3a,7a-Dihydrobenz-imidazole Nucleus and Its Preliminary Chemistry Including a Novel Quinoline Construction.

R. BOESE

R. BOESE

Dep. Chem., Univ. Calif., Berkeley, CA 94720, USA

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H.-J. + KNOELKER

H.-J. + KNOELKER

Dep. Chem., Univ. Calif., Berkeley, CA 94720, USA

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K. P. C. VOLLHARDT

K. P. C. VOLLHARDT

Dep. Chem., Univ. Calif., Berkeley, CA 94720, USA

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First published: January 12, 1988

Abstract

The title addition of the alkynes (II) or (V) to the imidazole (I) regioselectively yields the compounds (IVa) or (VI) as major or sole products.

ChemInform Abstract

The title addition of the alkynes (II) or (V) to the imidazole (I) regioselectively yields the compounds (IVa) or (VI) as major or sole products. The structure of (IVa) is confirmed by X-ray analysis (space group P21/c with Z=4). (VIc) is transformed to the title quinoline derivative (X) via demetalation, aromatization and imine hydrolysis.

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