1421852-10-9Relevant academic research and scientific papers
In Situ Generated TEMPO Oxoammonium Salt Mediated Tandem Cyclization of β-Oxoamides with Amine Hydrochlorides for the Synthesis of Pyrrolin-4-ones
Zhao, Xuna,Liu, Tong-Xin,Ma, Nana,Zhang, Guisheng
, p. 6125 - 6132 (2017/06/23)
A novel in situ generated TEMPO oxoammonium salt mediated one-pot tandem reaction has been developed for the straightforward construction of pyrrolin-4-ones from readily available β-oxoamides with amine hydrochlorides. The reaction tolerates various functional groups and represents a reliable method for the synthesis of highly substituted pyrrolin-4-ones in good yields under mild conditions. Detailed mechanistic studies disclosed that TEMPO oxoammonium salt generated in situ was crucial for the transformation involving the formation of enaminone precursors in situ by condensation of the β-oxoamides with amines, followed by sequential oxidative coupling with β-oxoamides, intramolecular cyclization, and 1,2-alkyl migration steps.
Cu(TFA)2-catalyzed oxidative tandem cyclization/1,2-alkyl migration of enamino amides for synthesis of pyrrolin-4-ones
Zhang, Zhi-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 4822 - 4825 (2013/10/08)
A novel Cu(TFA)2-catalyzed oxidative tandem cyclization/1,2- alkyl migration of readily available enamino amides for the synthesis of pyrrolin-4-ones has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of substituted pyrrolin-4-ones in high yields under mild conditions.
Cu(ii)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones
Wang, Zikun,Bi, Xihe,Liao, Peiqiu,Liu, Xu,Dong, Dewen
supporting information, p. 1309 - 1311 (2013/03/14)
A novel Cu(ii)-catalyzed cyclization of α-diazo-β-oxoamides with amines has been developed, constituting a straightforward method to construct pyrrol-3(2H)-one rings. The intramolecular hydrogen bonding effect in α-diazo-β-oxoamides plays an essential role in this reaction. A plausible reaction mechanism involving divergent generation and subsequent [2 + 3] cyclization of ketene and α-diazoimine intermediates was proposed.
