Synthesis of new tetrahydronaphthyl-1,2,4-triazines of potential antibacterial activity

ABSTRACT

The present work emphasized the syntheses of new asymmetric triazines incorporated at position -5 with a tetrahydronaphthyl moiety which is known by its inhibitory effect on anaerobic glycolysis[1] The desired compounds were obtained by allowing 6-acetyl-tetraline [2] to undergo selenium dioxide oxidation to give the corresponding tetralyl glyoxal [1]. This upon reaction with methylthiosemicarbazide hydrogen iodide, cyclization occurred to give 3-methylthio-5-[l,2,3, 4-tetrahydronaphth-6-yl]-l,2,4-triazine [2]. The [1]H NMR of 2 [Delta ppm, CDCl[3]] revealed 8 protons [m,m] of four methylenes of the tetraline ring at 1.82,2.90; 3 protons [s] of SCH[3] at 2.7 and 4 aromatic protons [m] at 7.1-7.9 ppm. The IR spectrum of 2 showed bands at 1600 cnr1[C=N] and at 1570-1480 cm[-1][C=C]