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Reissert indole synthesis : ウィキペディア英語版
Reissert indole synthesis
The Reissert indole synthesis is a series of chemical reactions designed to synthesize indole or substituted-indoles (4 and 5) from ortho-nitrotoluene 1 and diethyl oxalate 2.〔Noland, W. E.; Baude, F. J. ''Organic Syntheses'', Coll. Vol. 5, p. 567 (1973); Vol. 43, p. 40 (1963). ((Article ))〕
Potassium ethoxide has been shown to give better results than sodium ethoxide.
==Reaction mechanism==
The first step of the synthesis is the condensation of o-nitrotoluene 1 with a diethyl oxalate 2 to give ethyl o-nitrophenylpyruvate 3. The reductive cyclization of 3 with zinc in acetic acid gives indole-2-carboxylic acid 4. If desired, 4 can be decarboxylated with heat to give indole 5.

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