3421-18-9Relevant academic research and scientific papers
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.
Reaction of 2-amino-2-cycloalken-1-one derivatives with p-benzoquinones, III
Kucklander,Kuna,Schneider
, p. 415 - 419 (1993)
Reaction of 1 with 2a yields the spirocyclic benzoxazine 3a, by-product is a 2,3-bisadduct 4. Quinone 6 is isolated from the reaction of 1b with 2b. 8 and 9a react to yield the benzofurane 11, which is acetylated to the hydroquinone derivative 14 and transformed to 13, respectively. Reaction of 8 with 9b yields 7a. 16a,b are obtained from 8 or 1 with 15. 16a is acetylated to 16c and split into 17a.
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.
Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones "in-Water" and their biological evaluation as antibacterial and antifungal agents
Tandon, Vishnu K.,Kumar, Sandeep,Mishra, Nripendra N.,Shukla, Praveen K.
, p. 375 - 386 (2013/01/15)
Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio)cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa- 2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929.
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.
