1848-46-0Relevant articles and documents
Claimed 2,1-benzisoxazoles are indazalones
Kurth, Mark J.,Olmstead, Marilyn M.,Haddadin, Makhluf J.
, p. 1060 - 1062 (2005)
(Chemical Equation Presented) Claims, by two groups, to have prepared 2,1-benzisoxazole derivatives are corrected to show that the products are indazalones (5). In addition, a simple preparation of 3-oxysubstituted 2H-indazole, by an unrecognized method i
Photocatalyst-free Synthesis of Indazolones under CO2 Atmosphere
Yang, Tianbao,Lu, Huiai,Qiu, Renhua,Hong, Ling,Yin, Shuang-Feng,Kambe, Nobuaki
supporting information, p. 1436 - 1442 (2019/03/26)
A convenient photocatalyst-free method for the synthesis of redox-active 1,2-dihydro-3H-indazol-3-one derivatives from (2-nitroaryl)methanol and amines was developed. The reaction proceeded efficiently at room temperature by irradiation of UV light under CO2 atmosphere (1.0 atm, flow) without any photocatalysts or additives. This mild, operationally simple method shows wide functional tolerance. The carbamate formed in situ from CO2 and amine is proposed to be the key of this reaction. Some of these compounds synthesized by the present method were found to exhibit high anticancer activities, which can lower the viability of cancerous cell lines such as HeLa, MCF-7 and U87.
N-N Bond Formation between Primary Amines and Nitrosos: Direct Synthesis of 2-Substituted Indazolones with Mechanistic Insights
Zhu, Jie S.,Kraemer, Niklas,Shatskikh, Marina E.,Li, Clarabella J.,Son, Jung-Ho,Haddadin, Makhluf J.,Tantillo, Dean J.,Kurth, Mark J.
, p. 4736 - 4739 (2018/08/24)
A concise, one-step route to indazolones from primary alkyl amines and o-nitrobenzyl alcohols is reported. The key step in this readily scalable indazolone forming process involves base-mediated in situ o-nitrobenzyl alcohol → o-nitrosobenzaldehyde conversion. Although this functional group interconversion is known to be useful for 2H-indazole synthesis, its reactivity was modulated for indazolone formation.