THE FORMATION OF ACYLAMINO-DERIVATIVES OF INDOLES AND PYRROLES BY REACTIONS WITH NITRILIUM SALTS
N-Methylnitrilum fluoroborates are prepared rapidly by warming trimethyloxonium fluoroborate wiht a slight excess of the nitrile, subsquent addition of indoles and pyrroles at low temperatures (-50 deg C to -20 deg C) gives iminium salts (and hence ketones) in high yields.
Reactions of nitrilium salts with indole and pyrrole and their derivatives in the synthesis of imines, ketones and secondary amines
Abstract Reactions of N-methyl- and N-ethyl-nitrilium salts with indole and pyrrole and their derivatives yield imines or imine salts in good yields. The related imines are obtained from the salts after careful basification and hydrolysis of the imine salts or the imines by heating with aqueous base give the related ketones in good yields. Alternatively, the imine salts can be reduced using sodium borohydride in methanol to give the related secondary amines.
Giles, Robert G.,Heaney, Harry,Plater, M. John
p. 7367 - 7385
(2015/08/24)
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