6788-68-7Relevant articles and documents
A Combined Experimental–Theoretical Study on Diels-Alder Reaction with Bio-Based Furfural: Towards Renewable Aromatics
van Scodeller,De Oliveira Vigier, Karine,Muller, Eric,Ma, Changru,Guégan, Frédéric,Wischert, Raphael,Jér?me, Fran?ois
, p. 313 - 323 (2020/10/19)
The synthesis of relevant renewable aromatics from bio-based furfural derivatives and cheap alkenes is carried out by using a Diels-Alder/aromatization sequence. The prediction and the control of the ortho/meta selectivity in the Diels-Alder step is an important issue to pave the way to a wide range of renewable aromatics, but it remains a challenging task. A combined experimental-theoretical approach reveals that, as a general trend, ortho and meta cycloadducts are the kinetic and thermodynamic products, respectively. The nature of substituents, both on the dienes and dienophiles, significantly impacts the feasibility of the reaction, through a modulation on the nucleo- and electrophilicity of the reagents, as well as the ortho/meta ratio. We show that the ortho/meta selectivity at the reaction equilibrium stems from a subtle interplay between charge interactions, favoring the ortho products, and steric interactions, favoring the meta isomers. This work also points towards a path to optimize the aromatization step.
Probing Carbocatalytic Activity of Carbon Nanodots for the Synthesis of Biologically Active Dihydro/Spiro/Glyco Quinazolinones and Aza-Michael Adducts
Majumdar, Biju,Mandani, Sonam,Bhattacharya, Tamalika,Sarma, Daisy,Sarma, Tridib K.
, p. 2097 - 2106 (2017/02/26)
Herein, we report the fluorescent carbon dots as an effective and recyclable carbocatalyst for the generation of carbon-heteroatom bond leading to quinazolinone derivatives and aza-Michael adducts under mild reaction conditions. The results establish this nanoscale form of carbon as an alternative carbocatalyst for important acid catalyzed organic transformations. The mild surface acidity of carbon dots imparted by -COOH functionality could effectively catalyze the formation of synthetically challenging spiro/glycoquinazolinones under the present reaction conditions.