58536-45-1

Upstream product

• 58870-09-0 6-methyl-2,4-diphenyl-1,6-dihydropyrimidine 
• 60050-48-8 3-benzamido-2-butenoic acid ethyl ester 
• 77202-10-9 4-methyl-6-phenyl-1,2,3-triazine 
• 100-47-0 benzonitrile 
• 67-64-1 acetone 
• 70769-72-1 1-phenyl-3-ethylsulfenyl-2-buten-1-one 
• 618-39-3 benzamidin 
• 1670-14-0 benzamidine monohydrochloride 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 1402611-18-0 benzyl (Z)-(3-oxo-1-phenylbut-1-en-1-yl)carbamate 
• 55-21-0 benzamide 
• 935-00-2 trans-4-phenyl-2-butene 
• 13514-79-9 6-methyl-2-phenylpyrimidin-4-ol 

Downstream Products

• 97085-38-6 2,6-Diphenyl-4-styryl-pyrimidin 

Relevant academic research and scientific papers

Selective synthesis of pyrimidines from cinnamyl alcohols and amidines using the heterogeneous OMS-2 catalyst

Herein, an efficient aerobic oxidative synthesis of pyrimidines was carried out using cinnamyl alcohols and amidines catalyzed by manganese oxide octahedral molecular sieve (OMS-2). The heterogeneous catalytic method features base-/additive-free conditions, wide substrate scope, use of O2 as a green oxidant, and simple operation. Moreover, the OMS-2 catalyst prepared by the conventional reflux method demonstrates catalytic selectivity, activity, and excellent recyclability.

Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C-H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.

Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives

Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines was illustrated with three examples of the Suzuki-Miyaura cross-coupling of the prepared tosylates with phenylboronic acid.

Cu-Catalyzed [3 + 3] Annulation for the Synthesis of Pyrimidines via β-C(sp3)-H Functionalization of Saturated Ketones

A novel, efficient, and facile approach for the synthesis of structurally important pyrimidines has been successfully developed by Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones. This method provides a new protocol for the synthesis of pyrimidines by a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization via direct β-C(sp3)-H functionalization of saturated ketones followed by annulation with amidines.

Transition Metal Free Intermolecular Direct Oxidative C-N Bond Formation to Polysubstituted Pyrimidines Using Molecular Oxygen as the Sole Oxidant

Various polysubstituted pyrimidines are smoothly formed via a base-promoted intermolecular oxidation C-N bond formation of allylic C(sp3)-H and vinylic C(sp2)-H of allyllic compounds with amidines using O2 as the sole oxid

2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: Synthesis and comparison of the optical properties

Condensation of donor-substituted aldehydes on methylpyrimidine led to two series of fluorescent molecules depending on the position of the methyl group. Whereas highly emissive 4-arylvinylpyrimidine derivatives are well-known, this is the first example of fluorescent 2-arylvinylpyrimidine compounds. The optical properties of the two families have been thoroughly compared. Whereas the series derived from 2-methylpyrimidine exhibit a blue shift in absorption and emission in comparison with 4-arylvinylpyrimidine, the influence of the position is less predictable on the fluorescence quantum yield. These compounds also exhibit halochromism: when adding acid, a bathotromic shift is observed in absorption whereas an increase of the fluorescence intensity which is red-shifted except for amino derivatives (a progressive quench of emission is observed in these cases). An emission solvatochromism study has shown that a higher intramolecular charge transfer seems to occur in 2-arylvinylpyrimidines than in 4-arylvinylpyrimidines.

Stereoselective and catalytic access to β-enaminones: An entry to pyrimidines

We describe herein a highly stereoselective access to Cbz-protected β-enaminones 2 based on the NaOH catalyzed rearrangement of propargylic hydroxylamines 1. The synthetic potential of these β-enaminones is illustrated in an original synthesis of pyrimidi

Stereoselective and catalytic access to β-enaminones: An entry to pyrimidines

We describe herein a highly stereoselective access to Cbz-protected β-enaminones 2 based on the NaOH catalyzed rearrangement of propargylic hydroxylamines 1. The synthetic potential of these β-enaminones is illustrated in an original synthesis of pyrimidi

The reaction of tetralones with nitriles: A simple approach to the synthesis of new substituted benzo[h]quinazolines, benzo[f]quinazolines and dibenzo[a,i]phenanthridines

The one-pot reaction of 1-tetralone with nitriles in the presence of triflic anhydride affords in good yields 2,4-disubstituted 5,6-dihydrobenzo[h] quinazolines, which oxidation with DDQ leads to the corresponding benzo[h]quinazolines. 2-Tetralone undergo

Highly efficient synthesis of pyrimidines under microwave-assisted conditions

Microwave irradiation of an amidine and alkynone in acetonitrile at 120°C gives 2,4-disubstituted and 2,4,6-trisubstituted pyrimidines in very high yield.