- A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of d-luciferin, starting from 1,4-benzoquinone
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2-Cyano-6-hydroxybenzothiazole is the key intermediate for the synthesis of d-luciferin, the natural substrate of firefly luciferases. A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with l-cysteine ethyl ester, followed by oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propan-oate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and a conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone). This nitrile reacts with d-cysteine to afford d-luciferin at room temperature in nearly quantitative yield (90-95%).
- Meroni, Giuseppe,Ciana, Paolo,Maggi, Adriana,Santaniello, Enzo
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- Synthesis of 2-substituted-6-hydroxy and 6-methoxy benzothiazoles from 1,4-benzoquinone
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A few 2-substituted-6-hydroxy and 6-methoxybenzothiazoles have been prepared from ethyl 6-hydroxybenzothiazole-2-carboxylate, obtained by oxidation of ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propanoate hydrochloride, in turn prepared from 1,4-benzoquinone.
- Meroni, Giuseppe,Rajabi, Mehdi,Ciana, Paolo,Maggi, Adriana,Santaniello, Enzo
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experimental part
p. 53 - 60
(2010/09/09)
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