Synthesis of Adamantane Derivatives. LVIII. Reaction of 1-Adamantyl Chloride with Some Heterocyclic Unsaturated Silanes

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概要

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• Various silylated heterocycles having amide functionality were treated with 1-adamantyl chloride (1) in the presence of a Lewis acid to give the corresponding N-adamantylated heterocycles. If α-position to the reacting lactim nitrogen was substituted, the reaction no longer occurred, or the adamantylation occurred at the position other than the expected nitrogen. These facts are attributed to a steric blocking effect of the α-substituent. While the same treatment of the thioamide 46 gave the S-adamantylated product, 48 and 51 afforded in contrast the N- and S-adamantylated products, respectively ; this result can be explained in terms of steric effect. Analogously, silylated 2-pyrazolines and triazoles were adamantylated at nitrogen. The reactions of 2-trimethylsilylthiophene, furan and -pyridine with 1 failed to give site-selective monoadamantylation.

• 公益社団法人日本薬学会の論文
• 1982-06-25

著者

• 佐々木 正

  Institute Of Applied Organic Chemistry Faculty Of Engineering Nagoya University

• 大野 正富

  Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University

• 大野 正富

  Institute Of Applied Organic Chemistry Faculty Of Engineering Nagoya University

• 中西 朗

  Institute of Applied Organic Chemistry, Faculty of Engineering, Nagoya University

• 中西 朗

  Institute Of Applied Organic Chemistry Faculty Of Engineering Nagoya University

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