Efficient and convenient synthesis of indazol-3(2H)-ones and 2-aminobenzonitriles.
A mild, efficient, one-pot protocol for the synthesis of indazole-3(2H)-ones via cyclization of nitro-aryl substrates through low-valent titanium reagent has been described. The method used Triethylamine (TEA) to control pH. Particularly, 2-aminobenzonitriles were synthesized by one step easily. The mechanistic course of the reaction suggests the involvement of an anion leading to an intramolecular cyclization via N-N bond formation.
Dou
Guolan
G
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.
Shi
Daqing
D
D020650:Combinatorial Chemistry Techniques / Q000379:methods; D018360:Crystallography, X-Ray; D003500:Cyclization; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007191:Indazoles; D009570:Nitriles; C014356:benzonitrile