25696-85-9

Upstream product

• 61541-41-1 6-azido-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 
• 18039-42-4 5-phenyl-2H-1,2,3,4-tetrazole 
• 93577-93-6 5-bromo-1,3-dimethyl-6-(1'-methylbenzylidenehydrazino)uracil 
• 78158-86-8 1,3-Dimethyl-5-(4-nitro-phenylazo)-6-{N'-[1-phenyl-meth-(Z)-ylidene]-hydrazino}-1H-pyrimidine-2,4-dione 
• 1128-14-9 5-amino-6-chloro-1,3-dimethyluracil 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 41661-91-0 6,8-dimethyl-4-oxy-3-phenyl-8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione 
• 52421-32-6 6-(benzylidene-1'-methylhydrazino)-1,3-dimethyluracil 
• 42285-76-7 6-Methyl-3-phenylpyrimido[5,4-e][1,2,4]triazine-5,7(6H,8H)-dione 
• 77-78-1 dimethyl sulfate 
• 32502-53-7 6-[N-[(E)-benzylideneamino]-N-methylamino]-3-methyl-1H-pyrimidine-2,4-dione 
• 25774-97-4 6-benzylidenehydrazino-1,3-dimethyluracil 
• 32502-63-9 3-phenyltoxoflavin 
• 164520-14-3 1-Cyclopentyl-6-methyl-3-phenyl-1H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione 

Downstream Products

• 118214-94-1 2,4a,5,6,7,8-hexahydro-3-phenyl-4a-(3-indolyl)-6,8-dimethylpyrimido<5,4-e><1,2,4>triazine-5,7-dione 

Relevant academic research and scientific papers

General syntheses of 1-alkyltoxoflavin and 8-alkylfervenulin derivatives of biological significance by the regioselective alkylation of reumycin derivatives and the rates of transalkylation from 1-alkyltoxoflavins into nucleophiles

Regioselective alkylations of reumycin derivatives under alkaline conditions with a dialkyl sulfate or alkyl halide in 1,4-dioxane or DMF to provide 1-alkyltoxoflavin or 8-alkylfervenulin derivatives of biological significance, are described. Namely, the primary and secondary alkylations of reumycin derivatives with appropriate dialkyl sulfates or alkyl bromides under alkaline conditions in 1,4-dioxane gave predominantly 1-alkyltoxoflavin derivatives, while the same alkylations in DMF instead of 1,4-dioxane gave predominantly 8-alkylfervenulin derivatives. In the case of tertiary alkylation, the reumycin derivative with 2-bromo-2-methylpropane in both solvents under the same conditions yielded only the 1-alkyltoxoflavin derivative. Moreover, the rates of transalkylation from 1-alkyltoxoflavin derivatives into nucleophiles, e.g. DMF and n-butylamine, are also described. That is, the toxoflavin derivatives possessing a primary alkyl group at the 1-position were easily dealkylated from the 1-position by heating with DMF, whereupon reumycin (i.e., 1-dealkyltoxoflavin, 8-dealkylfervenulin) derivatives were formed. In other words, transalkylation from the toxoflavin derivatives into DMF took place, However, the transalkylation of 1-alkyltoxoflavin derivatives possessing a secondary or tertiary alkyl group at the 1-position was not observed under such conditions. On the other hand, when heating 1-alkyltoxoflavin derivatives with n-butylamine in 1,4-dioxane, the transalkylations were more easily observed even in the case of 1-alkyltoxoflavin derivatives substituted by a tertiary alkyl group.

Facile and general syntheses of 1-alkyltoxoflavin and 8-alkylfervenulin derivatives of biological significance by the regiospecific alkylation of reumycin (1-demethyltoxoflavin, 8-demethylfervenulin) derivatives

Regiospecific alkylation of reumycins (6) under alkaline conditions with a dialkyl sulfate or alkyl halide in dioxane and in DMF to provide 1-alkyltoxoflavins (5) of biological significance and 8-alkylfervenulins (7), respectively, is described.

Further Studies on the Ring Transformation of Pyrimido-as-triazine 4-Oxides to Pyrrolopyrimidines Involving 1,3-Dipolar Cycloaddition Reactions

The reaction of 3-alkyl(or aryl)-6,8-dimethylpyrimido-as-triazine-5,7(6H,8H)-dione 4-oxides (1a-f) with ethyl phenylpropiolate (EPP) in toluene afforded the unexpected 6-alkyl(or aryl)-5-benzoyl-7-(ethoxy-carbonyl)-1,3-dimethylpyrrolopyrimid

N-Bromosuccinimide in Heterocyclic Synthesis. Synthesis of Pyrazolopyrimidines, Pyrimido-as-triazines, and Pyrimidopyridazines from 6-Arylidenehydrazino-1,3-dimethyluracil Derivatives

Reactions of 6-arylidenehydrazino-1,3-dimethyluracil derivatives with N-bromosuccinimide leading to pyrazolopyrimidines, pyrimido-as-triazines, and pyrimidopyridazines are described.

A NEW SYNTHESIS OF FERVENULINS AND ALLOXAZINES. THERMOLYSIS AND PHOTOLYSIS OF 6-AZIDO-1,3-DIMETHYLURACIL WITH TETRAZOLES AND BENZOTRIAZOLES

Thermolysis of 6-azido-1,3-dimethyluracil(1) in the presence of 5-substituted tetrazoles(2) gave 3-substituted fervenulins(4), which were also synthesized from the intermediates(3) prepared by photolysis of (1) with (2).Irradiation of (1) with benzotriazoles(6) in tetrahydrofuran gave 6-(benzotriazol-1-yl)uracils(7), which were irradiated in methanol to afford alloxazines (8).

A NEW SYNTHESIS OF PYRIMIDO-as-TRIAZINE DERIVATIVES

The reaction of 5-arylazo-6-arylidenehydrazino-1,3-dimethyluracils (II), prepared by the diazotization of 6-arylidenehydrazino-1,3-dimethyluracils (I), with dimethylformamide dimethylacetal afforded the corresponding 3-arylfervenulins (3-aryl-6,8-dimethylpyrimido-as-triazine-5,7(6H,8H)-diones) (V).