INTERACTION OF 2,4,6-TRINITROTOLUENE AND ITS ANALOGUES WITH ALDEHYDES. SYNTHESIS OF BENZOANNELATED HETEROCYCLES FROM THE PRODUCTS OF CONDENSATION

ABSTRACT 2,4,6-Trinitrotoluene (TNT) and its sulfonyl analogue 2-isobutylsulphonyl-4,6-dinitrotoluene undergo smooth condensation with chloral and fluoral to give 2-R-4,6-dinitrophenyl-1-(trihalomethyl)ethanols which easily cyclize to give 4-R-6-nitro-2-trihalomethyl-2,3-dihydrobenzo[b]furans (R=NO2, i-Bu; halogen = F or Cl) in the presence of K2CO3. 2-R′-sulphonyl-4,6-dinitrotoluenes, prepared from TNT, condense with aromatic aldehydes to form 1-(2-R′-sulphonyl-4,6-dinitro)-2-arylethenes in which the ortho-nitro group, upon interaction with NaN3 was selectively substituted by the azido group. Thermolysis of the obtained azides gave 2-aryl-4-R′-sulphonyl-6-nitroindoles (R′ = Ph, i-Bu, PhCH2). Such N-methylated indole (R′ = i-Bu) was regioselectively aminated.