Process for the preparation of luciferin compounds

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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C07D41704

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048269891

ABSTRACT:
The present invention provides a process for the preparation of compounds of the general formula: ##STR1## in which X is a hydroxyl group and X.sub.1 is a hydrogen atom or a hydroxyl group, and especially of luciferin, by the reaction of D-cysteine with 2-cyanomono- or -dihydroxybenzothiazole obtained from 2-chloromono- or -dimethoxybenzothiazole via a demethylation, wherein the demethylation is accomplished by reaction with iodotrimethylsilane or with a mixture of phenyltrimethylsilane and iodine and hydrolysis under mild conditions of the silyl derivative formed.

REFERENCES:
Fusor, Advanced Organic Chemistry, 178-81 (Wiley, 1950).
White et al., "Analogs of Firefly Luciferin", J. Org. Chem. 30, 2344-8 (1965).
Ho et al., "Spaltung von Esters und Ethers mit Iodotrimethylsilan", Argu. Chemie 15, 847 (1976).
Starks, "Phase-Transfer Catalysis. I. Heterogeneous Reactions, . . . ", J.A.C.S. 93, 195-9 (1971).

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