3421-18-9Relevant articles and documents
Crystal Structure of Morpholinium-2,3-dicyano-hydroquinolate [1]
Schoedel,Seitz,Bock,Bats
, p. 63 - 68 (1996)
On deprotonation of 2,3-dicyano-p-hydroquinone by morpholine, a network of hydrogen bonds is formed in which the chains of hydroquinone monoanions are connected by strong ⊕N H...O and by weak ⊕N H...N bonds via the morpholinium nitrogens.
Unprecedented Formation of 2,5-Diaminoquinones from the Reaction of Vanillin with Secondary Amines in Aerobic Conditions
Barbero, Mauro,Papillo, Valentina A.,Grolla, Ambra A.,Negri, Roberto,Travaglia, Fabiano,Bordiga, Matteo,Condorelli, Fabrizio,Arlorio, Marco,Giovenzana, Giovanni B.
supporting information, p. 136 - 139 (2019/12/27)
Vanillin is widely used as a flavoring agent in foods, perfumes and in several other applications. Even if huge amounts of vanillin are annually employed in these manufacturing processes, its reactivity is underexplored, especially for the formation of potentially toxic substances. In this context, we observed the formation of orange to red crystalline compounds in the reaction of vanillin with secondary amines in aerobic conditions. NMR and HRMS allowed identifying the products as 2,5-diamino-1,4-benzoquinones. Preliminary investigations of this reaction led to a proposed mechanism involving an oxidative fragmentation of vanillin as the key step. MTT tests did not show any toxic effect up to 0.1 mm.
Synthesis of 2,5-Diaminoquinones by one-pot copper-catalyzed aerobic oxidation of hydroquinones and addition reaction of amines
Kim, Sungjin,Kim, Daehwan,Park, Jaiwook
experimental part, p. 2573 - 2578 (2009/12/29)
The aerobic oxidation of various hydroquinones was achieved by using copper nanoparticles entrapped in aluminum oxyhydroxide [Cu/ AlO(OH)] at room temperature. Furthermore, 2,5diamino-1,4-benzoquinones were synthesized directly from hydroquinone and amines by a one-pot procedure consisting of the copper-catalyzed aerobic oxidation of hydroquinones and the double addition of amines to the resulting quinones.