Synthesis of N-acetyl-1,3-dimethyltetrahydroisoquinolines by intramolecular amidomercuration:: Stereochemical aspects

被引：13

作者：

de Koning, CB ^{[1
]}

Michael, JP ^{[1
]}

van Otterlo, WAL ^{[1
]}

机构：

[1] Univ Witwatersrand, Sch Chem, Inst Mol Sci, Johannesburg, South Africa

来源：

SYNLETT | 2002年 / 12期

关键词：

amidomercuration; cyclization; isoquinoline; Mitsunobu; rotamers;

D O I：

10.1055/s-2002-35594

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Mercury(II)-mediated ring closure of N-[1-(2-allyl-3 -benzyloxy-4,6-dimethoxyphenyl)ethyl] acetamide 4 afforded N-acetyl-5-benzyloxy-6,8-dimethoxy-1,3-trans-dimethyl-1,2,3,4-tetrahydroisoquinoline 3. The product was shown to exist as a mixture of rotamers by NMR spectroscopy, since signals coalesced at higher temperatures. 2-[2-[1-(Acetylamino)ethyl]-6-(benzyloxy)3,5-dimethoxyphenyl]-1-methylethyI rnethanesulfonate 8 was also cyclized with sodium hydride to afford rotameric products with the same isoquinoline skeleton, but as a mixture of 1,3-cis- and trans-dimethyl isomers.

引用

页码：2065 / 2067

页数：3

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