A novel synthesis of N1-(substituted)-pyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-diones (original) (raw)
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A novel synthesis of 3-(substituted)pyrimido[4,5-c]pyridazine-5,7(1H,6H)-diones
Tetrahedron Letters, 2010
An improved synthesis of 3-(substituted)pyrimido [4,5-c]pyridazine-5,7(1H,6H)-diones, a known subclass of 4-deazatoxoflavins, is reported. The approach involves treatment of 3-methyl-6-(1methylhydrazinyl) uracil with representative phenyl and alkyl glyoxal monohydrates, which in turn are obtained by selenium dioxide oxidation of the corresponding phenyl and alkyl methyl ketones. The first entry into 4-monosubstituted isomers is also reported.
ChemInform, 2010
A new route to substituted pyrimido[5,4-e]-1,2,4-triazine-5,7(1H,6H)-diones is outlined. The synthesis proceeds via pre-formed hydrazone intermediates, which are then condensed with an activated chlorouracil to build up the entire molecular framework, followed by a reductive ring closure to provide the parent series. The route has been extended to the isomeric pyrimido[5,4e]-1,2,4-triazine-5,7(6H,8H)-dione class via the use of methylhydrazine as hydrazine surrogate, followed by regiospecific alkylation of the N 8 -H pyrimidotriazinediones with a range of alkyl and alkaryl substituents. This new methodology permits the generation of a wide range of compounds with variable substitution at the N 1 , C 3 , and N 8 positions for a heterocyclic scaffold with demonstrated pharmacological activity.
HETEROCYCLES, 2009
Coupling of E-1-(1-methylbenzimidazol-2-yl)-3-(N,Ndimethylamino)prop-2-enone (1) with the arenediazonium salt gave hydrazonopropanal 5 which underwent cyclocondensation with active methylene compounds to afford substituted pyridazin-6-imine 8 and 11. The enaminone 1 coupled also with the diazonium salts prepared from aminopyrazole, aminotriazole and 2-amino-1H-benzimidazole to afford pyrazolo[5,1-c]-l,2,4triazine 15, 1,2,4-triazolo[5,1-c]-1,2,4-triazine 19, 1,2,4-triazino[4,3a]benzimidazole 23 derivatives, respectively.
Journal of Chemical Research
The condensation reaction of 6-acetyl-3-amino-5-aryl-2-phenyl-2,5-dihydropyridazine-4-carbonitrile with triethyl orthoformate and then with hydrazine hydrate to obtain the new fused bicyclic 4-aryl-5-hydrazinyl-3-(1-hydrazonoethyl)-1-phenyl-1,4-dihydropyrimido[4,5-c]pyridazines via the Dimroth rearrangement is reported. Further cyclisation was achieved by the treatment of latter compounds with triethyl orthoformate to afford several derivatives of a novel tetracyclic fused system [1,2,4] triazolo[4′′,3′′:1′,6′]pyrimido[4′,5′:3,4]pyridazino[1,6-d][1,2,4]triazine.
Journal of Chemical Research, 2015
The condensation reaction of 6-acetyl-3-amino-5-aryl-2-phenyl-2,5-dihydropyridazine-4-carbonitrile with triethyl orthoformate and then with hydrazine hydrate to obtain the new fused bicyclic 4-aryl-5-hydrazinyl-3-(1-hydrazonoethyl)-1-phenyl-1,4dihydropyrimido[4,5-c]pyridazines via the Dimroth rearrangement is reported. Further cyclisation was achieved by the treatment of latter compounds with triethyl orthoformate to afford several derivatives of a novel tetracyclic fused system triazolo[4′′,3′′:1′,6′]pyrimido[4′,5′:3,4]pyridazino[1,6-d ][1,2,4]triazine.
Synthesis of Potentially Bioactive Hydrazones of Pyrimidine and 1,3,5-Triazine
AgriScience and Technology, 2021
The reaction of the pyrimidine and 1,3,5-triazine hydrazides with various aldehydes formed corresponding hydrazones. Synthesized compounds are endowed with potential bioactivity. In laboratory-vegetation screening, the obtained compounds showed a pronounced stimulating effect on plant growth. The activity of the tested compounds varied in the range of 46–88 % as compared to heteroauxin. Compounds that showed an activity above 70 % in the experiment will be selected for deeper study and further field tests.
ARKIVOC, 2011
2-Aryl-4,5-dioxopyrrolidine-3-carboxylate and 5-aryl-2,4-dioxopyrrolidine-3-carboxylate derivatives were successfully synthesized via carbonyl-based multiple component reaction and Dieckmann cyclization, respectively. Successive functional group transformations which include decarboxylation and hydrazonation afforded 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4hydrazone derivatives. Compound 3d exhibited activity against human histiocytic lymphoma (U937) and neuroblastoma (SH-SY5Y) cell lines while compound 6 showed neuroprotective ability from oxidative stress medium induced with H 2 O 2 .
Arkivoc, 2009
3-Hydrazino-2,7,8,9-tetrahydro-1H-benzo [6',7']cyclohepta[1',2':4,5] pyrido[2,3-d] pyrimidin-1one (5) was prepared in good yield by reaction of 3 or 4 with hydrazine hydrate under reflux. Reaction of compound 5 with different aldehydes in acetic acid gave the corresponding hydrazono derivatives 7. Cyclization of the latter compounds with bromine in acetic acid afforded a series of novel pentacyclic compounds namely, 5,6,7,11-tetrahydro-15Hbenzo[6'',7'']cyclohepta[1'',2'':4',5']pyrido[2',3'-d][1,2,4] triazolo[4,3-a]pyrimidin-15-ones (11af). In addition, reaction of compound 5 with β-diketones and α-diketone were investigated. The structures of the so formed compounds were confirmed by elemental and spectral analyses (1 H NMR, 13 C NMR, IR and MS).