4436-63-9

Upstream product

• 1633-67-6 2-chlorocyclohept-1-ene-1-carbaldehyde 
• 77287-34-4 formamide 
• 290-87-9 1,3,5-Triazine 
• 14092-11-6 1-pyrrolidino-1-cycloheptene 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 502-42-1 cycloheptanone 
• 7182-08-3 4-(1-cyclohepten-1-yl)morpholine 
• 3473-63-0 formamidine acetic acid 
• 1135538-97-4 4-(1-hydroxycyclohexyl)-1-(4-methylbenzenesulfonyl)-1,2,3-triazole 
• 6313-33-3 formamidine hydrochloride 
• 78-27-3 1-Ethynylcyclohexan-1-ol 

Relevant academic research and scientific papers

COMPOUNDS AND METHODS FOR TREATING CANCER

Substituted hydrazone compounds, methods of making such compounds and metal complexes thereof, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds and metal complexes to treat, prevent or ameliorate cancer are provided.

Direct access to pyrimidines through organocatalytic inverse-electron-demand Diels-Alder reaction of ketones with 1,3,5-triazine

An organocatalytic inverse-electron-demand Diels-Alder reaction of ketones with 1,3,5-triazine through enamine catalysis has been developed. This method could furnish 4,5-disubstituted pyrimidines in good yields and high levels of regioselectivities.

Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenone derivatives and cycloalkanones depending on the electron density/ring size of the ketone

3-Methyl-5-nitro-4-pyrimidinone undergoes two kinds of nucleophilic type ring transformations upon treatment with cycloalkanones in the presence of ammonium acetate, which affords 4,5-disubstituted pyrimidines and 5,6-disubstituted 3-nitro-2-pyridones. In order to improve the synthetic utility of this reaction, it is necessary to control the regioselectivity of these ring transformations. In the present work, we performed DFT calculation to realize the selectivity of two ring transformation products. In cases of adduct intermediates derived from cyclohexanone and cyclooctanone, the 2-attack proceeds preferably to give condensed pyrimidines. On the other hand, the adduct intermediate derived from cycloheptanone undergoes the 4-attack predominantly to afford condensed nitropyridone.

Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N -Sulfonyl-1,2,3-triazol-4-yl)alkanols

Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl)

One-step synthesis of 4,5-disubstituted pyrimidines using commercially available and inexpensive reagents

4,5-Disubstituted pyrimidines are synthesized from the corresponding ketone in one-step using inexpensive reagents (formamidine acetate, n-propanol, heat). Contrasted to other methods, this process appears quite amenable to large-scale use in industrial settings.

Palladium-catalysed synthesis of pyrimidines

Satisfactory yields of 4-substituted pyrimidines and bicyclic pyrimidines are produced from α-methyl or α-methylene ketones when reacted with formamide and tetrakis(triphenylphosphine)palladium(0) or a 1:2 mixture of palladium(II) acetate and triphenylphosphine as catalysts. Under the same reaction conditions pyridines or imidazole are formed from 1,3- or 1,2-diketones.

Two ring transformations of 3-methyl-5-nitropyrimidin-4(3H)-one for the construction of azaheterocycles

The reaction of 3-methyl-5-nitropyrimidin-4(3H)-one with ketones in the presence of NH3 afforded 4,5-disubstituted pyrimidines 5. Use of ammonium acetate instead of NH3 as the nitrogen source caused another ring transformation giving 5,6-disubstituted 3-nitro-2-pyridones 8 as well as 5. Pyrimidinone 1 behaved as an activated diformylamine 6 in the former reaction and as the synthetic equivalent of α-nitroformylacetic acid 9 in the latter case. The ratio of 5 and 8 produced when using NH4OAc varied with solvent. The reaction in acetic acid predominantly afforded pyrimidine 5, but in methanol the reaction afforded pyridone 8. The two types of ring transformations presented here are novel methods for the preparations of azaheterocycles.

Novel ring transformation of nitropyrimidinone; synthetic equivalent of α-nitroformylacetic acid

3-Methyl-5-nitropyrimidin-4(3H)-one reacts with ketones in the presence of ammonium salts to afford disubstituted pyrimidines and disubstituted 3-nitro-2-pyridones in a novel ring transformation reaction; nitropyrimidinone behaves as an activated diformylamine in the former case, and as a synthetic equivalent of α-nitroformylacetic acid in the latter case.