Reductive coupling of hydantoins with benzophenones by low-valent titanium: Synthesis of 4-substituted 1H-imidazol-2(3H)-ones and unusual two-to-two coupled products |
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Authors: | Naoki Kise Shuta Goi Toshihiko Sakurai |
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Institution: | Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan |
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Abstract: | The reductive coupling of 1,3-dimethyhydantoin with benzophenones by TiCl4-Zn in THF gave 4-diarylmethyl-1H-imidazol-2(3H)-ones as four-electron reduced one-to-one coupled products and their dimers as two-to-two coupled products predominantly by controlling the reaction conditions. The reductive coupling of 5-alkyl-1,3-dimethyhydantoins with benzophenones produced 5-alkyl-4-diarylmethyl-1H-imidazol-2(3H)-ones as the sole products irrespective to the reaction conditions. On the other hand, the reductive coupling of 1,3-dimethyhydantoin with cyclic benzophenones selectively 4-arylhydroxymethyl-1H-imidazol-2(3H)-ones as two-electron reduced one-to-one coupled products and they were further reduced to 4-diarylmethyl-1H-imidazol-2(3H)-ones. |
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Keywords: | Reductive coupling Low-valent titanium Hydantoins Aromatic ketones Corresponding author |
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