✦ LIBER ✦

Synthesis and reactivity of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole

✍ Scribed by Elisa M. Woolridge; Steven E. Rokita

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 290 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93319-2

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✦ Synopsis

The N-l BOC protected precursors of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole were prepared and deprotected via flash vacuum thermolysis.

The stability of these newly prepared, unprotected indole derivatives has been characterized and compared to that of a previously known compound, 6-(trifluoromethyl)indole.

The tryptophan processing enzymes, tryptophanase and tryptophan synthase, catalyze the reversible C-3 alkylation of indole through a mechanism proposed to include N-l deprotonation.' Synthetic work in our laboratory has been directed at developing substrate analogues for the characterization of this basedependent event.

Halomethyl-containing compounds have proven useful in the identification of carbanionic intermediates formed during enzyme turnover: and a similar analysis may be applicable to our heteroatomic system. Accordingly, we have developed syntheses for 6-(fluoromethyljindole and 6-(difluoromethyl)indole.

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