A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′-benzothiazolyl)-thiazole-4-carboxylic acid] from 1, 4-benzoquinone

P Ciuffreda, S Casati, G Meroni, E Santaniello

Index: Ciuffreda, Pierangela; Casati, Silvana; Meroni, Giuseppe; Santaniello, Enzo Tetrahedron, 2013 , vol. 69, # 29 p. 5893 - 5897

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Citation Number: 3

Abstract

A new synthesis of dehydroluciferin [2-(6′-hydroxy-2′-benzothiazolyl)-thiazole-4- carboxylic acid], the oxidative product of luciferin, has been realized starting from 1, 4- benzoquinone. Reaction of this compound with l-cysteine ethyl ester, followed by an oxidation–cyclization step afforded 2-carbethoxy-6-hydroxybenzothiazole that was in situ hydrolyzed and decarboxylated to 6-hydroxybenzothiazole. The tert-butyl (dimethyl) silyl ...