Journal
TETRAHEDRON
Volume 61, Issue 28, Pages 6801-6807Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.04.069
Keywords
2-aminoindans; synthesis; 2-azidoindans; 2-indanols; Mitsunobu reactions; dopamine
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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.
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