Concise syntheses of 2-aminoindans via indan-2-ol |
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Authors: | Sü leyman Gö ksu,Hasan Seç en |
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Affiliation: | Department of Chemistry, Faculty of Arts and Sciences, Ataturk University, 25240 Erzurum, Turkey |
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Abstract: | ![]() 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 Br2 afforded 2-amino-5,6-dibromoindan. |
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Keywords: | 2-Aminoindans Synthesis 2-Azidoindans 2-Indanols Mitsunobu reaction Dopamine |
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