39260-04-3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 53170-68-6 o-<(triphenylphosphoranyliden)amino>benzaldehyde 
• 26908-38-3 pyrimido[4,5-b]quinoline-2,4-(1H,3H)-dione 
• 74-88-4 methyl iodide 
• 7278-51-5 6-anilino-1,3-dimethyluracil 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 67387-23-9 1,3-dimethyl-6,7,8,9-tetrahydroquinolino<2,3-d>pyrimidine-2,4-(1H,3H)-dione 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 62-53-3 aniline 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 5344-90-1 2-Aminobenzyl alcohol 
• 28795-61-1 6-chloro-1,3-dimethyl-4-N-phenylcytosine 
• 28795-56-4 6-anilino-1,3-dimethyl-4-phenylimino-3,4-dihydro-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Catalytic Acceptorless Dehydrogenation of Amino Alcohols and 2-Hydroxybenzyl Alcohols for Annulation Reaction under Neutral Conditions

A base-free and acceptorless Ru-catalyzed dehydrogenative approach has been developed for the synthesis ofN-heterocycles by using 1,3-dicarbonyls and amino alcohols through a domino sequential enamine formation and intramolecular oxidative cyclization strategy. This unified approach is also applicable for the synthesis of O-heterocycles involving 2-hydroxybenzyl alcohol as a coupling reactant via consecutive C-alkylation and intramolecular cyclization steps. The present protocol is general for the synthesis of varieties of biologically important scaffolds, such as tetrahydro-4H-indol-4-one, 3,4-dihydroacridin-1(2H)-one, and tetrahydro-1H-xanthen-1-ones derivatives using a single catalytic system, viz. RuH2CO(PPh3)3. Environmentally benign H2O and H2are the only byproducts in this domino process. Moreover, RuH2CO(PPh3)3-catalyzed C3-alkylation of tetrahydro-4H-indol-4-one using alcohol as a alkylating partner is also described in this report. For the first time, a solvent-free gram-scale reaction for the acceptorless dehydrogenative annulation has been demonstrated. A plausible mechanism for the Ru-catalyzed base-free and acceptorless dehydrogenative annulation of amino alcohols or 2-hydroxybenzyl alcohols has been provided with several experimental investigations and spectroscopic evidence.

Synthesis of pyrimidine fused quinolines by ligand-free copper-catalyzed domino reactions

Herein, we report two novel methods for the synthesis of pyrimidine fused quinolines using a one-pot C-C and C-N bond forming strategy from the reaction of 6-aminouracils with 2-bromobenzaldehydes or 2-bromobenzyl bromide derivatives in the presence of 10 mol % CuCl2 without using any ligand. The reaction of 2-bromobenzaldehyde or its derivatives with 6-aminouracils in the presence of K2CO3 as base and a catalytic amount of CuCl2 in DMF medium under microwave heating conditions provides corresponding pyrimidine fused quinoline derivatives in good yields within 30 min. Alternatively, pyrimidine fused quinoline derivatives have been synthesized from the reaction of 2-bromobenzyl bromides with 6-aminouracil derivatives in the presence of molecular oxygen, CuCl2 (10 mol %), and K2CO3 as base in DMF under reflux conditions. Structures of all the products were unambiguously confirmed by spectroscopic techniques and by recording single crystal XRD of 3a.

Study of photophysical properties of 5-deazaalloxazine and 1,3-dimethyl-5-deazaalloxazine in dependence of pH using different spectral techniques

The photophysical properties of 5-deazaalloxazine and 1,3-dimethyl-5-deazalloxazine at different pH values were characterized using absorption spectra, fluorescence emission spectra, fluorescence excitation spectra, synchronous fluorescence spectra and total fluorescence spectra. Their ionised and/or neutral forms were discussed in comparison with those obtained for other derivatives of 5-deazaalloxazine and/or 5-deazaisoalloxazine. Steady-state and time-resolved techniques were used to study the protonation/deprotonation equilibria between cationic and neutral forms of both compounds and between neutral and monoanionic forms of 5-deazalloxazine, as well as between monoanionic forms of this compound and its dianion. We estimated pKa values for these equilibria both in the ground and excited states. Our steady-state and time-resolved measurements indicate that the cation of 5-deazaalloxazine in its isoalloxazinic form exhibits fluorescence that is quenched by protons in a dynamic process. Contrary to that, the cation of 1,3-dimethyl-5-deazaalloxazine has almost no fluorescence. Additionally, we found that the neutral forms of 5-deazalloxazine and 1,3-methyl-5-deazalloxazine are also quenched in acidic conditions by protons. In basic conditions, 5-deazaalloxazine forms two structurally different anions, namely the alloxazinic monoanion and the isoalloxazinic monoanion; both simultaneously dissociate into the isoalloxazinic dianion at even higher pH values. The synchronous fluorescence spectra and total fluorescence spectra demonstrated their suitability to characterize and differentiate different fluorescent forms of 5-deazalloxazine, namely: the cation, the neutral form, two monoanions, and the dianion, in a wide pH range.

Cascade imination, Buchwald-Hartwig cross coupling and cycloaddition reaction: Synthesis of pyrido[2,3-d]pyrimidines

A novel and efficient palladium catalyzed method was developed for the synthesis of wide range of pyrido[2,3-d]pyrimidines, using readily available β-bromovinyl/aryl aldehydes and 6-amino-1,3-dialkyluracils as the starting materials with good yields. This reaction proceeds via cascade imination/Buchwald-Hartwig cross coupling/cycloaddition reactions under microwave irradiation and solvent free conditions. This journal is

Ring closure reactions of cyclic 2-arylaminomethylene-1,3-diones

5-Arylaminomethylene compounds such as 5-arylaminomethylenepyrimidine-2,4,6-triones 2 or 2-phenylaminomethylenephenalene-1,3-dione 13 cyclize by thermolysis via migration of the arylamino group to pyrimido[4,5-b]quinoline-2,4-diones 6 or 7-oxo-7H-naphtho[

A facile entry to fused pyrimidines: Preparation of pyrimido[4,5-b]quinoline and pyrido[2,3-d:6,5-d']dipyrimidine derivatives

A number of pyrimido[4,5-b]quinolines 3 and pyrido[2,3-d:6,5-d']-dipyrimidines have been prepared by reaction of N,N'-disubstituted barbituric acids with the iminophosphorane derived from o-azidobenzaldehyde or 6-amino-5-formyl-1,3-dimethyluracil.

Reaction of Enaminones with Carbon Disulfide: Synthesis of Heterocycles Using Enamino Dithiocarboxylates

Reaction of various types of enaminones, which are prepared by the condensation of 1,3-dicarbonyl compounds with aromatic amines, with carbon disulfide in the presence of sodium hydroxide as the base in dimethyl sulfoxide to give the corresponding enamino

Friedlaender Condensations of o-Aminobenzaldehyde with Hydroxypyridines

Condensations of o-aminobenzaldehyde (1) with 2,6-dihydroxypyridines under Friedlaender conditions result in the formation of the benzonaphthyridines 6a and 6b.The reaction of 1 with 2,4,6-trihydroxypyridine-3-carbonitrile (4) yields the expected 1,3(2H,5H)-dioxobenzonaphthyridin-4-carbonitrile (7).The 4-hydroxy-2(1H)-oxobenzonaphthyridin-3-carbonitrile (8a) was also isolated.N-Methylation and substitution of the ring systems with alkyl groups which allow cyclisation reactions to be carried out, are also reported.

Pyrimidine Derivatives and Related Compounds. XLVI. Thermal and Photochemical Transformation of 5-Substituted 6-Azido-1,3-dimethyluracils into Fused Pyrimidines such as Isoxazolopyrimidines, Pyrazolo-pyrimidines, and Pyrimido-t

Thermolysis and photolysis of 6-azido-1,3-dimethyluracils possessing certain substituents (formyl, benzoyl, hydrazonomethyl, phenyl, and benzyl groups) at the 5-position provided new methods for the preparation of fused pyrimidines.Irradiation and heating