6851-79-2Relevant articles and documents
Synthesis of glycolurils and hydantoins by reaction of urea and 1, 2-dicarbonyl compounds using etidronic acid as a “green catalyst”
Bakibaev, Abdigali A.,Uhov, Artur,S. Malkov, Victor,Yu. Panshina, Svetlana
, p. 4262 - 4270 (2020/10/02)
Most of the known methods for the synthesis of heterocyclic compounds have disadvantages, such as a long reaction time and aggressive conditions. We have developed a new, rather simple and efficient method for the synthesis of a number of glycoluryls and hydantoins in water using a etidronic acid (HEDP) as “Green catalyst.” So, for the first time, the condensation reaction of ureas with 1, 2-dicarbonyl compounds was carried out in the presence of HEDP. Also based on NMR studies, a chemism of these reactions, which is stepwise, is proposed. It has been established that the optimal conditions for the synthesis of glycoluryls and hydantoins using HEDP are: temperature 80°C-90°C, 40-20 minutes, and the ratio of urea and HEDP is 1:1. In all cases, the remaining aqueous filtrate containing HEDP after the reaction can be reused for other cycles synthesis of glycoluril and other compounds, because HEDP is not converted during the reaction.
3-(Triflyloxy)benzynes Enable the Regiocontrolled Cycloaddition of Cyclic Ureas to Synthesize 1,4-Benzodiazepine Derivatives
Kaneko, Hideki,Ikawa, Takashi,Yamamoto, Yuta,Arulmozhiraja, Sundaram,Tokiwa, Hiroaki,Akai, Shuji
supporting information, p. 943 - 948 (2018/02/26)
A versatile synthesis of 1,4-benzodiazepine derivatives through the reaction of various 3-(trifluoromethanesulfonyloxy)benzynes with N -(p -toluenesulfonyl)imidazolidin-2-ones is reported. This reaction system provides a 1,4-benzodiazepine bearing a trifluoromethanesulfonyloxy group as a single regioisomer among the four possible regioisomers.
NOVEL AMIDE DERIVATIVE AND USE THEREOF AS MEDICINE
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Paragraph 0789; 0790; 0791, (2013/03/26)
Provided are a novel low-molecular-weight compound that suppresses production of induction type MMPs, particularly MMP-9, rather than production of hemostatic type MMP-2, as well as a prophylactic/therapeutic drug for autoimmune diseases or osteoarthritis. An amide derivative represented by the following formula (I) wherein each symbol is as defined in the specification, or a pharmacologically acceptable salt thereof.
Facile synthesis of hydantoins and thiohydantoins in aqueous solution
Baccolini, Graziano,Boga, Carla,Delpivo, Camilla,Micheletti, Gabriele
experimental part, p. 1713 - 1717 (2011/05/05)
A series of hydantoins and thiohydantoins have been synthesized in water at room temperature from urea (or N-methylurea, or thiourea) and simple aldehydes (as glyoxal, and its simple derivatives) in the presence of phosphoric anhydride. The reaction time is 10 min using an equimolar amount of P 4O10 with respect to the other reagents, but the reaction occurs also, even if with longer reaction times, with very small amounts of P4O10. In addition, this method provides a clean and 'green' approach to hydantoins, compounds of great interest in biological and pharmacological fields.
BASE CATALYZED CYCLIZATION OF SUBSTITUTED ESTERS OF HYDANTOIC AND THIOHYDANTOIC ACID
Kavalek, Jaromir,Machacek, Vladimir,Svobodova, Gabriela,Sterba, Vojeslav
, p. 375 - 390 (2007/10/02)
Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol.The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place.Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions.The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30percent of the starting ester.In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis.Substituents always accelerate the cyclization.The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium.The cyclizations are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.
Pyrimidine Derivatives and Related Compounds. Part 50. Photochemical Reaction of 5-Substituted 6-Azido-1,3-dimethyluracils with Nucleophiles. Ring Transformation of Pyrimidine to 1,3,5-Triazepine and Hydantoin Ring Systems
Hirota, Kosaku,Maruhashi, Kazuo,Kitamura, Norihiko,Asao, Tetsuji,Senda, Shigeo
, p. 1719 - 1723 (2007/10/02)
Photolysis of 5-substituted 6-azidouracil derivatives in the presence of nucleophiles has been studied.Irradiation of 5-alkyl-6-azidouracils (3) in the presence of amines caused a ring expansion to give 1,3,5-triazepine derivatives (7).Photolysis of 6-azi
α-Functionalized Amino Acid Derivatives. A Synthetic Approach of Possible Biogenetic Importance
Herscheid, Jacobus D. M.,Nivard, Rutger J. F.,Tijhuis, Marian W.,Scholten, Henk P. H.,Ottenheijm, Harry C. J.
, p. 1880 - 1885 (2007/10/02)
A new and efficient approach of general applicability to the synthesis of α-functionalized α-amino acid derivatives 3 is described.It is based upon the proposal that the biosynthesis of such compounds might occur via oxidation of an N-acylated amino acid
