10229-53-5Relevant articles and documents
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Tanimoto,S. et al.
, p. 627 - 628 (1979)
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One-pot synthesis of oxime ethers from benzaldehyde or acetophenone, hydroxylamine salt, potassium hydroxide, and alkyl halides
Li, Chunbao,Zhang, Hang,Cui, Yi,Zhang, Shuanming,Zhao, Zheyuan,Choi, Michael C. K.,Chan, Albert S. C.
, p. 543 - 546 (2003)
Oxime ethers were synthesized in one-pot reaction from benzaldehyde or acetophenone, hydroxylamine hydrogen chloride, alkyl halides and KOH in aqueous DMSO. The reactions were completed in 15-50 min with yields in 80-96%.
Change of Orientation in Electrophilic Substitution of Benzaldehydes by O-Alkyloximation Derivatives
Goda, Hiroshi,Ihara, Hirotaka,Hirayama, Chuichi,Sato, Makoto
, p. 1565 - 1568 (1994)
By the introduction of O-alkyloxyimino group, orientation in electrophilic substitution of benzaldehyde can be selectively controlled.
A Short Total Synthesis of Benzophenanthridine Alkaloids via a Rhodium(III)-Catalyzed C-H Ring-Opening Reaction
Aravindan, Narasingan,Jeganmohan, Masilamani
, p. 14826 - 14843 (2021/10/20)
The biologically important naturally available benzophenanthridines were prepared efficiently in three steps with overall good yields. A new synthetic methodology involving a rhodium(III) catalyzed redox-neutral ring-opening of 7-azabenzonorbornadienes with aromatic aldoximes is developed to synthesize the target molecules. The developed C-H ring-opening reaction is highly diastereoselective and compatible with various sensitive functional group substituted aromatic aldoximes as well as substituted 7-azabenzonorbornadienes. The ring-opening products were transformed into highly sensitive 13,14-dehydrobenzo phenanthridine derivatives by HCl hydrolysis. Subsequently, 13,14-dehydrobenzophenanthridines were converted into biologically important benzophenanthridine alkaloids in the presence of DDQ. A possible reaction mechanism was proposed for the C-H ring-opening reaction and supported by the deuterium labeling studies.
Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids
Hao, Hong-Yan,He, Yu-Ting,Lou, Shao-Jie,Luo, Gen,Mao, Yang-Jie,Xiong, Xue,Xu, Dan-Qian,Xu, Zhen-Yuan
supporting information, p. 6732 - 6737 (2020/09/21)
A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.
