Schiff's bases prodn. from 1-amino 3-phenylindole - by reaction with aldehydes, useful as bacteriostats and fungistats

摘要

Prepn. of Schiff's bases of formula (I) (X=2-5C aliphatic gp. or a 5-6 membered carbocylic or heterocyclic ring at least partly unsatd., opt. attached via a 1-4C aliphatic bridging gp.; the carbocyclic rings are opt. substd.) comprises reacting corresp. 1-amino-3-phenylindol (II) with XCHO with water elimination. Opt. (I) is then converted to a salt. (I) are low-toxicity fungistats and bacteriostats useful in medicine and plant protection. Pref. X include phenyl substd. by alkoxy and/or dialkylaminoalkoxy. The reaction of 10.3g (II) with 7.8g vanillin gave 13.5g (80%) 1-(p-hydroxy-m-methoxybenzylideneamino)-3-phenylindole. This was converted (in 75% yield) by Na or Et2NCH2CH2Cl to the p-diethylaminoethoxy cpd.