Process for the preparation of 3-unsubstituted indoles using met

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

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546178, 548502, C07D20910, C07D40312

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active

051571226

ABSTRACT:
An indole having the formula I: ##STR1## is prepared by a Fischer-Indole reaction employing a mixture of phosphorous pentoxide and methane sulfonic acid as an acid catalyst. The reaction, which is optionally run in a co-solvent, provides 3-unsubstituted indoles in high yields with high regioselectivity. The indole thus prepared is an intermediate in the synthesis of leukotriene biosynthesis inhibitors.

REFERENCES:
P. E. Eaton et al., Phosphorous Pentoxide-Methanesulfonic Acid, J. Org. Chem. 38, 4071 (1973).
A. Guy and J. P. Guette, Utilization of Polyphosphoric Acid Synthesis, 1980, 222.
H. Illy and L. Funderburk, Fisher Indole Syn. Direction of Cyclization, J. Org. Chem., 33, 4283 (1968).
M. H. Palmer and P. S. McIntyre, Fischer Indole Syn. Unsymmetrical Ketones, J. Chem. Soc. (B), 1969, 446.

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