Serial double nucleophilic addition of amines to the imidazole nucleus
β Scribed by Shunsaku Ohta; Tomohisa Osaki; Satoko Nishio; Akemi Furusawa; Masayuki Yamashita; Ikuo Kawasaki
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 590 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
2-(1-Chloro-2,2-dimethylpropyl)-1-methyl-1H-imidazole hydrochloride (2aβ’HCl) was treated with an excess of N,N-dimethylamine at room temperature to give an abnormal addition product, 4,5-bis
The former might be evolved from a serial double nucleophilic addition of the secondary amine molecules to the imidazole nucleus, which has been generally considered as an electron-excessive and stable aromatic ring.
π SIMILAR VOLUMES
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Nucleophilic conjugate addition of benzylamine to 2-hydroxyalkylpropenoates la-c proceeds in high yield with modest diastereoselection. However, addition of benxylamine to the silyl ether of lc produces only the anti-isomer 2d in high yield Although nucleophilic conjugate additions of amines to 2-su