39258-93-0

Usage

Structure

Nitro-substituted pyridine derivative with a phenyl group attached to the 6-position of the pyridine ring

Usage

Organic synthesis, pharmaceutical research, development of pharmaceutical drugs and agrochemicals

Biological activities

Potential antifungal and antimicrobial properties

Versatility

Building block in the synthesis of various heterocyclic compounds, used in the preparation of potential drug candidates

Upstream product

• 98-86-2 acetophenone 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 98-80-6 phenylboronic acid 
• 27048-04-0 2-amino-6-chloro-3-nitropyridine 
• 92138-35-7 6-chloro-3-nitro-1H-pyridin-2-one 
• 102266-15-9 2-amino-3-nitro-6-phenylpyridine 
• 1556-32-7 1,3-dinitroquinolizin-4-one 

Downstream Products

• 66336-01-4 1-methyl-3-nitro-6-phenylpyridin-2(1H)-one 
• 161029-97-6 2-methoxy-3-nitro-6-phenylpyridine 
• 1439394-30-5 tert-butyl(1-(4-((3-amino-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamate 
• 187242-88-2 2-chloro-3-nitro-6-phenylpyridine 
• 1439394-28-1 tert-butyl (1-(4-((3-nitro-6-phenylpyridin-2-yl)amino)phenyl)cyclobutyl)carbamate 
• 1313881-69-4 tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate 
• 1313881-70-7 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine 

Relevant academic research and scientific papers

PROCESS OF PREPARING 3-(3-(4-(1-AMINOCYCLOBUTYL)PHENYL)-5-PHENYL-3H-IMIDAZO[4,5-B]PYRIDIN-2-YL)PYRIDIN-2-AMINE

The present invention is directed to a processes for the synthesis of 3-(3-(4-(1-aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine:

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.

Novel synthesis of bihetaryl compounds

The ring transformation of nitropyrimidinone 1 with acetophenone derivatives 2 affords two kinds of azaheterocyclic compounds, 4-phenylpyrimidines 3 and 3-nitro-6-phenyl-2-pyridones 4. On the basis of the relationship between electronic properties of the substituent and ratios of products, a plausible reaction mechanism is provided. Furthermore, the present reaction could be applied to heterocyclic ketones giving bihetaryl compounds.

Synthetic equivalent of α-nitroformylacetic acid

A novel synthetic procedure for 3-nitro-2-pyridone derivatives (2) is provided, which includes the ring transformation of 1,3-dinitroquinolizin-4-one (3) with ketones in the presence of ammonium acetate.

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.