28735-27-5Relevant academic research and scientific papers
Comparison of non-covalent interactions and spectral properties in 1-methyl-3-methylthio-5-phenyl-1,2,4-triazinium mono- and tetraiodide crystals
Yushina, Irina D.,Rudakov, Boris V.,Stash, Adam I.,Bartashevich, Ekaterina V.
, p. 1981 - 1991 (2019)
The reaction of 1-methyl-3-methylthio-5-phenyl-1,2,4-triazinium (MTPT) iodide with diiodine in a solution leads to monoiodide crystal structure that in excess of iodine gives the unusual tetraiodide anion with two central iodine atoms in disorder. The bonding within the anion has been characterized as I–…I2…I–; the existence of the bound iodine molecule inside has been proven by the characteristic band in experimental and calculated Raman spectra. Non-covalent interactions of MTPT in considered crystal structures are different. Monoiodide anion as a strong electron donor allows the formation of the S…I chalcogen bonds that are absent in tetraiodide structure. The features of halogen bonds within the I4 2– anion are?also performed.
Selective N1/N4 1,4-Cycloaddition of 1,2,4,5-Tetrazines Enabled by Solvent Hydrogen Bonding
Zhu, Zixi,Glinkerman, Christopher M.,Boger, Dale L.
, p. 20778 - 20787 (2020/12/22)
An unprecedented 1,4-cycloaddition (vs 3,6-cycloaddition) of 1,2,4,5-tetrazines is described with preformed or in situ generated aryl-conjugated enamines promoted by the solvent hydrogen bonding of hexafluoroisopropanol (HFIP) that is conducted under mild reaction conditions (0.1 M HFIP, 25 °C, 12 h). The reaction constitutes a formal [4 + 2] cycloaddition across the two nitrogen atoms (N1/N4) of the 1,2,4,5-tetrazine followed by a formal retro [4 + 2] cycloaddition loss of a nitrile and aromatization to generate a 1,2,4-triazine derivative. The factors that impact the remarkable change in the reaction mode, optimization of reaction parameters, the scope and simplification of its implementation through in situ enamine generation from aldehydes and ketones, the reaction scope for 3,6-bis(thiomethyl)-1,2,4,5-tetrazine, a survey of participating 1,2,4,5-tetrazines, and key mechanistic insights into this reaction are detailed. Given its simplicity and breath, the study establishes a novel method for the simple and efficient one-step synthesis of 1,2,4-triazines under mild conditions from readily accessible starting materials. Whereas alternative protic solvents (e.g., MeOH vs HFIP) provide products of the conventional 3,6-cycoladdition, the enhanced hydrogen bonding capability of HFIP uniquely results in promotion of the unprecedented formal 1,4-cycloaddition. As such, the studies represent an example of not just an enhancement in the rate or efficiency of a heterocyclic azadiene cycloaddition by hydrogen bonding catalysis but also the first to alter the mode (N1/N4 vs C3/C6) of cycloaddition.
Synthesis of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazines that have antibacterial activity and also inhibit inorganic pyrophosphatase
Lv, Wei,Banerjee, Biplab,Molland, Katrina L.,Seleem, Mohamed N.,Ghafoor, Adil,Hamed, Maha I.,Wan, Baojie,Franzblau, Scott G.,Mesecar, Andrew D.,Cushman, Mark
, p. 406 - 418 (2014/01/17)
Inorganic pyrophosphatases are potential targets for the development of novel antibacterial agents. A pyrophosphatase-coupled high-throughput screening assay intended to detect o-succinyl benzoic acid coenzyme A (OSB CoA) synthetase inhibitors led to the unexpected discovery of a new series of novel inorganic pyrophosphatase inhibitors. Lead optimization studies resulted in a series of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazine derivatives that were prepared by an efficient synthetic pathway. One of the tetracyclic triazine analogues 22h displayed promising antibiotic activity against a wide variety of drug-resistant Staphylococcus aureus strains, as well as activity versus Mycobacterium tuberculosis and Bacillus anthracis, at a concentration that was not cytotoxic to mammalian cells.
NITROGEN HETEROCYCLE DERIVATIVES, PREPARATION THEREOF AND APPLICATION THEREOF IN HUMAN THERAPEUTICS
-
Paragraph 0229; 0230, (2013/03/26)
The present invention relates to compounds having general formula I characterised in that wherein in particular: R1 represents one or a plurality of groups such as: trifluoromethyl, halogen such as F, Cl, Br, methyl, nitro. R represents nitroge
1,2,4-TRIAZINE-4-AMINE DERIVATIVES
-
Page/Page column 97; 98, (2011/09/14)
According to the invention there is provided a compound of formula A1 which may be useful in the treatment of a condition or disorder ameliorated by the inhibition of the A1- A2b or, particularly, the A2a receptor wherein the compound of formula A1 has the structure, wherein, A represents Cy1 or HetA; Cy1 represents a 5- to 14-membered aromatic, fully saturated or partially unsaturated carbocyclic ring system comprising one, two or three rings, which Cy1 group is optionally substituted by one or more R4a substituents; HetA represents a 5- to 14-membered heterocyclic group that may be aromatic, fully saturated or partially unsaturated, and which contains one or more heteroatoms selected from O, S and N, which heterocyclic group may comprise one, two or three rings and which HetA group is optionally substituted by one or more R4b substituents; B represents a Cy2 or HetB; Cy2 represents a 3- to 10-membered aromatic, fully saturated or partially unsaturated carbocyclic ring system comprising one or two rings, which Cy2 group is optionally substituted by one or more R4c substituents; HetB represents a 3- to 10-membered heterocyclic group that may be aromatic, fully saturated or partially unsaturated, and which contains one or more heteroatoms selected from O, S and N, which heterocyclic group may comprise one or two rings and which HetB group is optionally substituted by one or more R4d substituents.
Polysubstituted 2,3-dihydrofuro[2,3-b]pyridines and 3,4-dihydro-2H-pyrano[2,3-b]pyridines via microwave-activated inverse electron demand Diels-Alder reactions
Hajbi, Youssef,Suzenet, Franck,Khouili, Mostafa,Lazar, Said,Guillaumet, Gérald
, p. 8286 - 8297 (2008/02/07)
Polysubstituted 2,3-dihydrofuro[2,3-b]pyridines and 3,4-dihydro-2H-pyrano[2,3-b]pyridines have been synthesized from 1,2,4-triazines using the inverse electron Diels-Alder reaction. For this purpose, 3-methylsulfanyl-1,2,4-triazines were reacted with seve
A general approach to selective functionalization of 1,2,4-triazines using organometallics in palladium-catalyzed cross-coupling and addition reactions
Alphonse, France-Aimee,Suzenet, Franck,Keromnes, Anne,Lebret, Bruno,Guillaumet, Gerald
, p. 2893 - 2899 (2007/10/03)
A selective way to obtain disubstituted 1,2,4-triazines in good yields by combining addition reactions and palladium-catalyzed cross-coupling reactions of organometallics with 3-methylsulfanyl-1,2,4-triazine is described.
Rapid synthesis of triazine inhibitors of inosine monophosphate dehydrogenase.
Pitts, William J,Guo, Junqing,Dhar, T G Murali,Shen, Zhongqi,Gu, Henry H,Watterson, Scott H,Bednarz, Mark S,Chen, Bang Chi,Barrish, Joel C,Bassolino, Donna,Cheney, Daniel,Fleener, Catherine A,Rouleau, Katherine A,Hollenbaugh, Diane L,Iwanowicz, Edwin J
, p. 2137 - 2140 (2007/10/03)
A series of novel triazine-based small molecule inhibitors (IV) of inosine monophosphate dehydrogenase was prepared. The synthesis and the structure-activity relationships (SAR) derived from in vitro studies are described.
STUDIES ON as-TRIAZINE DERIVATIVES. X. ADDITION REACTION OF PHENYLMAGNESIUM BROMIDE WITH 1,2,4-TRIAZINES
Konno, Shoetsu,Sagi, Mataichi,Yoshida, Nobuko,Yamanaka, Hiroshi
, p. 3111 - 3114 (2007/10/02)
The reaction of 1,2,4-triazine with phenylmagnesium bromide was investigated.Every position 3,5, and 6 in a 1,2,4-triazine ring is active in the addition reaction of Grignard reagents.Since 5-phenyl-1,2,4-triazine, 5,6-diphenyl-1,2,4-triazine, and 3,5,6-t
FURTHER INTRAMOLECULAR DIELS-ALDER REACTIONS OF 1,2,4-TRIAZINES. SYNTHESIS OF DIHYDROPYRROLOpyridines
Taylor, Edward C.,Pont, Joseph L.
, p. 379 - 382 (2007/10/02)
3-(3-Butynylamino)-1,2,4-triazines undergo intramolecular Diels-Alder reactions to yield 2,3-dihydropyrrolopyridines
