Synthesis and Characterization of Novel Compounds Derived From 6-methyl-2,6 dihydro[1,2,4-triazino[4,3-b] indazol-3(4H)-one.

The parent compound (6-methyl-2,6 dihydro[1,2,4-triazino[4,3-b]indazol-3(4H)-one was prepared from reaction of ((1-Methyl-1H-indazol-3-yl)-hydrazine) with ethyl bromoacetate, then (41) new compounds were synthesized. The first compound (1) was synthesized from condensation of parent compound with 2-chloro benzaldehyde in basic medium, after that novel compounds was derived from chalcone (1). Five, six and seven member ring were produced from cyclized of α,β unsaturated system with several materials such as (malononitrile, ethyle cyanoacetate, 2-amino phenol, 2-amino thiophenol, phenylene diamine mercapto acetic acid, phenyl hydrazine, ect) to offered (1-15) derivatives. The pyridazine and pyridazinone compounds (17-20) were synthesized from treatment of parent compound with dimethyl amine, methyl amine, chloro acetyl chloride and formic acid, respectively while derivative (21) produced from reaction of (20) with urea by. Besides that, compound (19) was a good key to synthesize oxazol, thiazol, thiazine and hydrazino derivatives (22, 23, 24 and 25) respectively. Hydrazino derivative (25) was also used for synthesis (26-28) derivatives. In additional to that, derivative (2) was a worthy core and a key intermediate for the synthesis of several new fused heterocycles in this work. Acylation of amino group in (2) with acetic anhydride was gave (29), while (2) cyclized with chloroacetic acid or malononitrile aes affered (30, 31) respectively. On the other side, amino group of (2) underwent to reaction with phenylisothiocyanate, ethylacetoacetate, urea, thiourea, phenylisothiocyanate and formamide to produce (32, 33, 34, 35, 37 and 38). While when derivative (2) cyclized with ethyl chloroacetate led to formation (36). Compound (2) was cyclized under heating with formamide, formic acid to give pyrimidine and pyrimidinone derivatives (39, 40) respectively. Finally, in presence of ethanol and hydrochloric acid, derivative (33) underwent to ring closure to produce (41). The structures, of all synthesized compounds were confirmed by using spectroscopic analysis such as UV, FTIR, 1H-NMR and 13CNMR spectral. [ABSTRACT FROM AUTHOR]