1220515-72-9Relevant academic research and scientific papers
Formation of 3-Aminophenols from Cyclohexane-1,3-diones
Szymor-Pietrzak, Damian,Khan, Muhammad N.,Pagès, Ana?s,Kumar, Ajay,Depner, Noah,Clive, Derrick L. J.
, p. 619 - 631 (2020/12/23)
meta-Aminophenols are formed by the action of DBU on 3-amino-2-chlorocyclohex-2-en-1-ones at room temperature in MeCN. The chloro compounds are generated by treating 3-aminocyclohex-2-en-1-ones with the easily prepared halogenating agent BnNMe3·ICl2 in Me
Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols
Bhattacherjee, Dhananjay,Thakur, Vandna,Shil, Arun K.,Das, Pralay
supporting information, p. 2202 - 2208 (2017/07/07)
A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis. (Figure presented.).
Synthesis of N-substituted carbazolones from α-iodo enaminones via Pd(0)-catalyzed intramolecular coupling under microwave irradiation
Yun, Xi-Liu,Bi, Wen-Ying,Huang, Jian-Hui,Liu, Yu,Zhang-Negrerie, Daisy,Du, Yun-Fei,Zhao, Kang
supporting information; experimental part, p. 5076 - 5080 (2012/09/25)
A variety of N-aryl and N-alkyl carbazolones were conveniently achieved in good to high yields via Pd2(dba)3-mediated intramolecular coupling of N-substituted α-iodo enaminones under microwave irradiation. The Pd(0)-catalyzed cyclization was found to proceed favorably with the more electron-deficient phenyl ring during the reactions involving unsymmetrical N,N-diaryl α-iodo enaminones. This unique property enables the construction of carbazolone skeleton containing nitro substituted benzenoid ring.
Concurrent α-iodination and N-arylation of cyclic β-enaminones
Chen, Yan,Ju, Tong,Wang, Junwei,Yu, Wenquan,Du, Yunfei,Zhao, Kang
supporting information; experimental part, p. 231 - 234 (2010/06/15)
A variety of N-substituted 3-aminocyclohex-2-enones were converted into the corresponding N-arylated α-iodo enaminones in high yields via concurrent N-iodination and N-arylation mediated by ArI(OAc)2. A mechanism is postulated to account for the reaction differences between the cyclic and the acyclic -enaminones, which undergo predominant β-acetoxylation under the same reaction conditions.
