84531-36-2

Usage

Uses

Used in Pharmaceutical Industry:
3-NITRO-6,7-DIHYDRO-5H-CYCLOPENTA[B]PYRIDINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
3-NITRO-6,7-DIHYDRO-5H-CYCLOPENTA[B]PYRIDINE is used as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its reactivity and ability to form various organic compounds contribute to the development of effective and targeted agrochemical products.
In both industries, the use of 3-NITRO-6,7-DIHYDRO-5H-CYCLOPENTA[B]PYRIDINE is driven by its potential to form a wide range of organic compounds, making it a versatile and valuable compound in the synthesis of pharmaceuticals and agrochemicals. However, due to its reactivity and potential hazards, it is crucial to handle 3-NITRO-6,7-DIHYDRO-5H-CYCLOPENTA[B]PYRIDINE with extreme care and follow strict safety protocols to ensure the safety of personnel and the environment.

InChI:InChI=1/C8H8N2O2/c11-10(12)7-4-6-2-1-3-8(6)9-5-7/h4-5H,1-3H2

Upstream product

• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 14080-32-1 5-nitropyrimidine 
• 1614-92-2 1-(N-piperidino)cyclopentene 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 14150-94-8 3,5-dinitro-1-methyl-2-pyridone 
• 120-92-3 cyclopentanone 
• 126215-88-1 5-nitro-2-(pent-4-yn-1-yl)pyrimidine 
• 108-94-1 cyclohexanone 

Downstream Products

• 178209-29-5 6,7-dihydro-5H-cyclopenta[b]pyridin-3-amine 
• 1421429-82-4 phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate 

Relevant academic research and scientific papers

Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine

The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. 1H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, 3CN, 23 °C, >95%).

An efficient synthesis of nitrated cycloalka[ b ]pyridines

The three-component ring transformation of 1-methyl-3,5-dinitro-2-pyridone with cycloalkanones of different ring sizes in the presence of ammonium acetate affords the corresponding nitrated cycloalka[b]pyridines in high yields. Furthermore, a double bond can be easily introduced into the product by changing the cycloalkanone into a cycloalkenone. Georg Thieme Verlag Stuttgart. New York.

SUBSTITUTED BICYCLIC AROMATIC CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS

The invention relates to substituted bicyclic aromatic carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

PREPARATION OF PYRIDINE DERIVATIVES USING PYRIMIDINIUM DERIVATIVES AS INTERMEDIATES

A method in which a pyridinium derivative of formula (I) such as 1,3-dimethyl-2,3-dihydro-2-oxopyrimidinium chloride is reacted with an acetyl compound of formula (II) such as 4-acetylpyridine, and then the reaction product is reacted with ammonia or an ammonium salt to form a pyridine derivative of formula (III):Also disclosed is a method for the preparation of the compound of formula (I) from reacting a compound of formula (IV) or (V) with a compound of formula (VI):Also disclosed are two additional alternative methods for the preparation of compounds of formula (I) and related compounds. The substituents are defined in the claims.

INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-(ALKYNYL)PYRIMIDINES AND 2-(ALKYNYL)PYRIDINES

Pyrimidines 3,7 and 13 carrying an ο-alkynyl side-chain -CR2(CH2)nCH2CCH (R=H, CN; n=1,2) at the 2-position undergo intramolecular inverse electron demand Diels-Alder reactions across the C-2 and C-5 positions.Loss of hydrogen cyanide, caused by a retro-Diels-Alder reaction, from the intermediate cycloadducts leads to annelated pyridines 5,9 and 15, respectively.Similarly, from the nitropyridines 16 the 2,3-dihydronitro-1H-indenes 18 are obtained.The influence of electronic and steric effects on the rate of cycloaddition is discussed.Gem-disubstitution on the chain connecting the reaction centers leads to a considerable rate enhancement for compounds 3 vs 13.Compounds 7, having an extra methylene group in the tether between diene and dienophile, react much slower than compounds 3 due to decreased entropic assistance.

INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 5-NITROPYRIMIDINE WITH ENAMINES. SYNTHESIS OF 3-NITROPYRIDINE DERIVATIVES

The reaction of cyclic and non-cyclic enamines with 5-nitropyrimidine has been studied.Many enamines react in an inverse electron-demand Diels-Alder reaction, leading to the formation of 3-nitropyridines.N,S-ketene acetals were also found to react with 5-nitropyrimidines.The mechanism of the reaction will be discussed.

RING TRANSFORMATIONS OF 5-NITROPYRIMIDINE VIA INVERSE DIELS-ALDER REACTIONS

5-Nitropyrimidine undergoes inverse Diels-Alder cycloadditions with ketene-N,N-, -O,O- acetals and enamines resulting in pyridine derivatives.The 1H NMR evidence for the 1-N,N-diethylaminopropyne cycloadduct formation is presented.