Synthesis And Properties Of 2H- Indazoles And 3-azolyl Quinolines

Most of multi-substituted indazole compounds have a strong biological and pharmaceutical activity, and most of them have been used as anticancer drugs, non-steroidal anti-inflammatory drugs, selective 5-HT3 receptor antagonists, guanylate cyclase activator, nitric oxide synthase inhibitors and calcium antagonists. Similarly, multi-substituted quinoline compounds have a high biological activities including antibacterial, anti-MRSA, antiallergenic, anti-alzheimer and anti-cancer activities. Therefore, the synthesis and study of these two classes of compounds have been favored by many scholars at home and abroad. In this paper, we use a sequential Ugi/nitrene insertion process to synthesize 3-(1H-tetrazolyl)-2H-indazoles. The synthesis conditions and the spectral properties of the target compounds are investigated. The Friedlander reaction was used to synthesize 3-azolyl quinoline compounds, and the biological activity of the target compounds was studied. Details are as follows:1. In this paper, we use aldehyde, primary amine and trimethyl silane azide and isonitrile as raw materials, to synthesize 3-(1H-tetrazolyl)-2H-indazoles by a sequential Ugi/nitrene insertion process.2. In this paper, we use 2-amino benzaldehyde and a-azolyl carbonyl compounds as raw materials, to synthesize 3-azolyl quinoline 4 by Friedlander reaction. The antibacterial activity of target compounds were tested, and most of the compounds have exhibited fungicidal activities. For example, compound 4h (R1= H, R2=Cl, R3=t-Bu, X = H) exhibits 100% and 98% inhibition activity against Penicilium digitatum and Fusarium graminearum in 50 ppm. Further activity test finds that the compound 4h still exhibits 65% inhibition activity against Fusarium graminearum even in 5 ppm.