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Novel nucleophilic CC bond‐forming tele ‐reaction of imidazole ring
Author(s) -
Ohta Shunsaku,
Sato Kentaro,
Kawasaki Ikuo,
Yamaguchi Yuko,
Nishio Satoko,
Yamashita Masayuki
Publication year - 2004
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570410305
Subject(s) - chemistry , imidazole , nucleophile , medicinal chemistry , ring (chemistry) , scope (computer science) , product (mathematics) , stereochemistry , catalysis , organic chemistry , geometry , mathematics , computer science , programming language
Reaction of 2‐(1‐chloro‐2,2‐dimethylpropyl)‐1‐methyl‐1 H ‐irnidazoles with diethyl methylmalonate in the presence of NaH gave a normal S N product, 2‐[(1,1‐diethoxycarbonylethyl)‐2,2‐dimethylpropyl]‐1‐methyl‐1 H ‐imidazole (2a) , and two tele ‐reaction products, 5‐(1,1‐diethoxycarbonylethyl)‐1‐methyl‐2‐(2,2‐dimethylpropyl)‐1 H ‐imidazole (3a) and trans ‐4,5‐di‐(1,1‐diethoxycarbonylethyl)‐4,5‐dihydro‐1‐methyl‐2‐(2,2‐dimethylpropyl)‐1 H ‐imidazole (4a) in 5, 17 and 70% yields, respectively. The scope and mechanism of this reaction are discussed.