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

详细信息    查看全文

• 作者：G??ksu ; S??leyman ; Se??en ; Hasan
• 关键词：2-Aminoindans ; Synthesis ; 2-Azidoindans ; 2-Indanols ; Mitsunobu reaction ; Dopamine
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：July 11, 2005
• 年：2005
• 卷：61
• 期：28
• 页码：6801-6807
• 全文大小：217 K

文摘

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 13;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 13;C catalyzed hydrogenation. The reaction of 2-aminoindan with 2.5 equiv Br₂ afforded 2-amino-5,6-dibromoindan.