80224-45-9Relevant academic research and scientific papers
Iminyl-radicals by electrochemical decarboxylation of α-imino-oxy acids: construction of indole-fused polycyclics
Wan, Jin-Lin,Cui, Jian-Feng,Zhong, Wei-Qiang,Huang, Jing-Mei
, p. 10242 - 10245 (2021/10/12)
Iminyl radicals are reactive intermediates that can be used for the construction of various valuable heterocycles. Herein, the electrochemical decarboxylation of α-imino-oxy acids for the generation of iminyl radicals has been accomplished under exogenous-oxidant- and metal-free conditions through the use ofnBu4NBr as a mediator. The resulting iminyl radicals undergo intramolecular cyclization smoothly with the adjacent (hetero)arenes to afford a series of indole-fused polycyclic compounds.
[3+2] Cycloadditions of α-acyl ketene dithioacetals with propargylamines: Pyrrole synthesis in water
Ren, Chuan-Qing,Di, Chong-Hui,Zhao, Yu-Long,Zhang, Jing-Ping
supporting information, p. 1478 - 1481 (2013/04/23)
A series of 2,3,4-trisubstituted and 1,2,3,4-tetrasubstituted pyrroles were synthesized via [3+2] cycloaddition of α-acyl ketene dithioacetals (or related substrates) with commercially available propargylamines as 1,3-dipoles in water. Most of the reactions can be performed in the absence of an external base. The reaction of secondary amine (N-methylprop-2-yn-1-amine) with α-acyl ketene dithioacetals showed different reaction behaviours depending on the addition or absence of an external base. Copyright
[3+2]Cycloaddition of propargylamines and α-acylketene dithioacetals: A synthetic strategy for highly substituted pyrroles
Zhao, Yu-Long,Di, Chong-Hui,Liu, Si-Di,Meng, Jia,Liu, Qun
supporting information, p. 3545 - 3550 (2013/02/23)
A new [3+2] cycloaddition strategy for the direct synthesis of highly substituted pyrroles from the readily available α-acylketene dithioacetals (or related substrates) and commercially available propargylamines under mild metal-free conditions has been developed. In this reaction, the acyl group plays a critical role in driving the conjugate addition of propargylamine and further cyclization to give pyrroles. Furthermore, the wide scope was confirmed by the preparation of 1,2,3,4-tetrasubstituted pyrroles (60-70% yields) via a formal 1,2-acyl migrating [3+2] cycloaddition pathway with N-methylprop-2-yn-1-amine as the secondary amine component.
N-propargylic β-enaminones: Common intermediates for the synthesis of polysubstituted pyrroles and pyridines
Cacchi, Sandro,Fabrizi, Giancarlo,Filisti, Eleonora
, p. 2629 - 2632 (2013/08/23)
N-Propargylic β-enaminones have been used as common intermediates for the synthesis of polysubstituted pyrroles and pyridines. Best results have been obtained using DMSO as solvent. In the presence of Cs2CO3 N-propargylic β-enaminone
Base-Induced Cycloaddition of N-(Tosylmethyl)imino Compounds to Michael Acceptors. Synthesis of 2,3,4-Trisubstituted Pyrroles
Houwing, Hendrik A.,van Leusen, Albert M.
, p. 1127 - 1132 (2007/10/02)
A series of N-(tosylmethyl)imino compounds has been prepared, and applied to a new, base induced, one operational synthesis of otherwise more difficulty accesible 2,3,4-trisubstituted pyrroles from electron deficient olefins.This regiospec
