Expedient Entry to 1-Aminoadamantane Derivatives via Aza-Prins Cyclization of 7-Methylenebicyclo[3.3.1]nonan-3-one Oximes

被引：6

作者：

Kuga, Tetsuya ^{[1
]}

Sasano, Yusuke ^{[1
]}

Tomizawa, Masaki ^{[1
]}

Shibuya, Masatoshi ^{[1
]}

Iwabuchi, Yoshiharu ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 09期

关键词：

1-aminoadamantanes; amantadine; 1-(alkoxyamino)-adamantanes; aza-Prins reaction; oxime; MEDICINAL CHEMISTRY; ADAMANTANE; OXIDATION; FUNCTIONALIZATION; ARYLATION; MEMANTINE;

D O I：

10.1055/s-0036-1591920

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of 1-aminoadamantane (amantadine) derivatives is described. This synthesis features acid-promoted aza-Prins cyclization of 7-methylenebicyclo[3.3.1]nonan-3-one oximes, which are readily prepared from 1,3-adamantanediol via a Grob fragmentation and the subsequent oximation, to give various 3-substituted 1-(alkoxyamino)adamantanes. After the reduction of alkoxyamines, not only 3-substituted 1-aminoadamantanes, but also chiral 2,5-disubstituted derivatives were obtained in good yields.

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页码：1820 / 1826

页数：7

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