Synthesis of Pyrazolo[3,4-b]quinoxaline Derivatives (Part I)

Journal of the Korean Chemical Society

Ho Sik Kim¹  Hyung Chul Lee¹ 

关键词: Pyrazolo[3;    4-b]quinoxalines;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

The reaction of 3-methoxycarbonylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline (7) with m-trifluoromethylbenzenediazonium chloride gave 3-[a-(m-trifluoromethylphenylhydrazono)methoxycarbonylmethyl]-1,2-dihydro-2-oxoquinoxaline (8), whose reaction with phosphoryl chloride provided 2-chloro-3-[a-(m-trifluoromethylphenylhydrazono)- methoxycarbonylmethylquinoxaline (9). The reaction of compound 9 with hydrazine hydrate resulted in the intramolecular cyclization to give 1-(m-trifluoromethylphenyl)-3-hydrazinocarbonyl-1H-pyrazolo[3,4-b]quinoxaline (10). The reaction of compound 10 with alkanoyl chlorides, benzaldehydes or isothiocyanates afforded 1H-pyrazolo[3,4-b]quinoxalines (12-14), respectively. Refluxing of compounds 14 in 2N NaOH solution gave the 1,2,4-triazolyl-1H-pyrazolo[3,4-b]quinoxalines (15). The reaction of compounds 13 with acetic anhydride were also cyclized to the 1,3,4-oxadiazolyl-1H-pyrazolo[3,4-b]quinoxalines (16).

【 授权许可】

Unknown