Concise syntheses of 2-aminoindans via indan-2-ol

被引：25

作者：

Göksu, S ^{[1
]}

Seçen, H ^{[1
]}

机构：

[1] Ataturk Univ, Dept Chem, Fac Arts & Sci, TR-25240 Erzurum, Turkey

来源：

TETRAHEDRON | 2005年 / 61卷 / 28期

关键词：

2-aminoindans; synthesis; 2-azidoindans; 2-indanols; Mitsunobu reactions; dopamine;

D O I：

10.1016/j.tet.2005.04.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Amino-5,6-dimethoxyindan hydrochloride was synthesized in seven steps and with an overall yield of 48%. Indan-2-ol was converted to 5,6-dibromo-indan-2-ol in three steps by acetylation, electrophilic bromination and deacetylation. Dimethoxylation of 5,6-dibromoindan-2-ol with NaOCH3 in the presence of CuI gave 5,6-dimethoxy-indan-2-ol, which was converted to 2-amino-5,6-dimethoxyindan hydrochloride by azidation, followed by Pd-C catalyzed hydrogenation. Similarly, 2-amino-5-bromoindan was synthesized in five steps and with an overall yield of 50%. Indan-2-ol was converted to 2-aminoindan by azidation followed by Pd-C catalyzed hydrogenation. The reaction of 2-aminoindan with 2.5 equiv Br-2 afforded 2-amino-5,6-dibromoindan. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6801 / 6807

页数：7

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