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[3H]2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalen (ADTN)

✍ Scribed by Yvonne Clement-Cormier; Charles E. Smith


Publisher
Springer
Year
1980
Tongue
English
Weight
624 KB
Volume
5
Category
Article
ISSN
0364-3190

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📜 SIMILAR VOLUMES


A Concise Synthesis of 2-Amino-1,2,3,4-t
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## Abstract 2‐Amino‐1,2,3,4‐tetrahydronaphthalene‐6,7‐diol (**2**; 6,7‐ADTN) was synthesized starting from naphthalene‐2,3‐diol in seven steps and with an overall yield of 44%. Methylation of naphthalene‐2,3‐diol with dimethyl sulfate, followed by __Friedel____Crafts__ acylation with AcCl, gave 2‐

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## Abstract Racemic 2‐amino‐1,2,3,4‐tetrahydronaphthalene‐5,6‐diol (5,6‐ADTN; **4**) was synthesized from 5,6‐dimethoxynaphthalene‐2‐carboxylic acid (**14**) in four steps (60% overall yield; __Scheme__). The crucial steps of the synthesis are __Birch__ reduction of **14** to the valuable synthon *

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A novel asymmetric route to 2-amino-1,2,3,4-tetrahydronaphthalenes has been demonstrated starting from phthalimidovinylglycinol (PVG). Functionalisation of PVG via Heck reaction, olefin hydrogenation and cyclisation provides the title products.