Synlett

A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1, 4-benzoquinone

G Meroni, P Ciana, A Maggi, E Santaniello

Index: Meroni, Giuseppe; Ciana, Paolo; Maggi, Adriana; Santaniello, Enzo Synlett, 2009 , # 16 p. 2682 - 2684

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Citation Number: 6

Abstract

Abstract 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) propanoate hydrochloride to 2-carbethoxy-6- ...