- Contributions to the Chemistry of Enaminoketones, XV: The Three-Component Synthesis of Hydrazinomethylene-chromandiones and a reductive N-N Bond Cleavage of Phenylhydrazine
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The three-component reaction of 4-hydroxycoumarin, ethylorthoformiate, and different substituted hydrazines is described. p-Nitrophenylhydrazine, hydrazides and phenylsemicarbazide lead to the expected hydrazinomethylene-chromandiones 2a-f.Reaction of 4-hydroxycoumarin, ethylorthoformiate, and phenylhydrazine or p-tolyl-hydrazine does not yield 2, but the anilino-methylene-chromandiones 6a-b.This indicates a reductive N-N bond cleavage to aniline and ammonia under mild conditions. - Keywords: Hydrazinomethylene-chromandiones; Reductive N-N bond cleavage; Anilinomethylenechromandiones
- Junek, H.,Reidlinger, C.
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- Discovery of two new classes of potent monoamine oxidase-B inhibitors by tricky chemistry
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The discovery of potent and selective monoamine oxidase-B inhibitors for the management of neurodegenerative diseases such as Alzheimer's and Parkinson's diseases is still a challenging endeavor. Herein, we report the discovery of two new classes of poten
- Cagide,Silva,Reis,Gaspar,Borges,Gomes,Low
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supporting information
p. 2832 - 2835
(2015/02/19)
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- POCl3-mediated synthesis of 2-N-arylimino-4-chloro-3- dichloromethylcoumarin and its conversion into 6H-[1]benzopyrano[4,3-b]quinolin- 6-one
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On heating in POCl3, 2-(N-aryl)aminochromone-3-carbaldehyde produced 2-N-arylimino-4-chloro-3-dichloromethylcoumarin, which undergoes selective acid-catalyzed hydrolysis of its imino function to produce 4-chioro-3-dichloromethylcoumarin. The hy
- Maiti, Sourav,Biswas, Pritam,Ghosh, Jaydip,Bandyopadhyay, Chandrakanta
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p. 1617 - 1623
(2014/01/17)
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- Exploring α-chromonyl nitrones as 1,5-dipoles
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N-Phenyl-C-chromonyl nitrones 1 and the allenoate zwitterion 2, generated by addition of phosphine to acetylenedicarboxylates, undergo a cascade reaction sequence involving an unprecedented [5+3] annulation followed by deoxygenative rearrangement leading to dihydropyridine-fused benzopyrones. Unusual electronic control by the N-substituents of 1 directs the annulation pathway, leading to two different ring-systems. Georg Thieme Verlag Stuttgart - New York.
- Wittstein, Kathrin,García, Ana B.,Schürmann, Markus,Kumar, Kamal
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supporting information; experimental part
p. 227 - 232
(2012/03/10)
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- Reaction of Amines on 3-Ureidomethylenecoumarins. A New Route to N-(Methylene-4-oxocoumarinyl)amines
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N-(Methylene-4-oxocoumarinyl)amines were prepared in good yield by reacting aliphatic and aromatic amines bearing functional groups with the relevant 3-ureidomethylenecoumarins.
- Hamdi, Maamar,Granier, Patrick,Sakellariou, Reine,Speziale Vincent
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p. 1155 - 1158
(2007/10/02)
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