- Synthesis of substituted (S)-2-aminotetralins via ring-opening of aziridines prepared from l-aspartic acid β-tert-butyl ester
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This paper describes the total synthesis of the hydrochloride salts of (2S)-2-amino-7-methoxytetralin (21-HCl) and (2S)-2-amino-6-fluoro-7- methoxytetralin (ST1214), from a common enantiomerically pure aziridine 4b, which was available from l-aspartic acid β-tert-butyl ester. The synthesis of 21-HCl and ST1214 proceeded in nine steps and 5 and 6% overall yields, respectively. Key steps are the regioselective ring-opening of 4b with ArMgBr/CuBr·SMe2 and the intramolecular Friedel-Crafts cyclisation providing α-tetralone. Substituted naphthalenes were formed as side products in the latter reaction.
- Aaseng, Jon Erik,Gautun, Odd R.
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scheme or table
p. 8982 - 8991
(2011/01/04)
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- Regioselective Monomethylation of Unsymmetrical Naphthalenediols with Methanolic HCl
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Treatment of naphthalene-1,3-diol and naphthalene-1,7-diol with methanol containing dry hydrogen chloride at room temperature gives exclusively 3-methoxy-1-naphthol and 7-methoxy-1-naphthol, respectively.Of the other two unsymmetrical naphthalenediols, the 1,2-isomer was unreactive and the 1,6-isomer gave a mixture of regioisomers under the same conditions.Two symmetrical diols (the 1,5- and 2,7-isomers) examined by the same procedure gave the monomethyl ethers in 60-70percent yields.
- Bell, Kevin H.,McCaffery, Leslie F.
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p. 731 - 737
(2007/10/02)
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- N-1H-tetrazol-5-yl-2-naphthalene carboxamides and their use as antiallergy and antiinflammatory agents
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Novel naphthalene derivatives having antiallergy and antiinflammatory activity.
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- Efficient syntheses of some 1-naphthylalkyl ketones and studies on their autooxidation in basic medium
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Birch reductions of 4,6-dimethoxy-1-naphthylalkyl ketones 1 provided in fair to good yields the demethoxylated products, 6-methoxy-1-naphthylalkyl ketones 2(a-g), not easily accessible by other procedures. Autooxidation of these ketones in basic medium afforded the diketones 6(a-c), the acid 2h, and interestingly the phenol 5. Extension of this reduction to the related tricyclic ketone 8 afforded 9a, the phenolic ketone 9b; and significantly the dihydrocoumarin derivative 10 as a result of autooxidation of 9a. The mechanisms for demethoxylation and autooxidation have been discussed.
- Chatterjee,Raychaudhuri,Chatterjee
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p. 3653 - 3660
(2007/10/02)
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