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KMID : 0370220060500060403
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Yakhak Hoeji
2006 Volume.50 No. 6 p.403 ~ p.408
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Efficient Synthesis of 2-Aminoindan and cis-(±)-4,4a,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one
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Kim Min-woo
Ma Eun-Sook
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Abstract
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1-Amino-5,6-dimethoxyindan hydrochloride was syntheiszed from 3-(3,4-dimethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with hydroxylamine, and reduction with an overall yield of 74%. 2-Amino-5,6-dimethoxyindan hydrochloride was synthesized from 3-(3,4-dimethoxyphenyl)propionic acid by intramolecular Friedel-Crafts acylation, oximation with isoamylnitrite, reduction in NaOH and reaction with HCl to form 5,6-dimethoxy-2-indanone,which was reacted with hydroxylamine and reduced with an overall yield of 42%. 5,6-dimethoxyindan-1,2-dione-2-oxime, which was catalytically hydrogenated to afford cis-, and trans-1-amino-5,6-dimethoxyindan-1-ol as 3:1 ratio. This mixture was treated with Li and reacted with chloroacetyl chloride. Cis isomer was acylated and cyclized to synthesize cis-(±)-7,8-dimethoxy-4,4a,5,9b-tetrahydroindeno [1,2-b][1,4]oxazin-3(2H)-one but trans isomer was just acylated to form amide.
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KEYWORD
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5,6-Dimethoxy-1indanone, 1-Aminoindan, 2-Aminoindan, cis-(±)-4,4,5,9b-tetrahydroindeno[1,2-b][1,4]oxazin-3(2H)-one
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