5693-62-9

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 4397, 1984 DOI: 10.1021/jo00197a013

InChI:InChI=1/C6H11NO/c1-8-6-4-2-3-5-7-6/h2-5H2,1H3

Upstream product

• 675-20-7 piperidin-2-one 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 10442-97-4 cyclopentanone oxime tosylate 
• 1192-28-5 Cyclopentanone oxime 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 368-39-8 triethyloxonium fluoroborate 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 109967-15-9 3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine 
• 1462-92-6 6-methyl-2,3,4,5-tetrahydro-pyridine 
• 99977-10-3 N-[2]piperidylidene-valine 
• 1604-01-9 6-propyl-2,3,4,5-tetrahydropyridine 
• 83688-89-5 6-(4-Pentenyl)-2,3,4,5-tetrahydropyridine 
• 2446-62-0 7,8,9-trihydropyrido[2,1-b]quinazolin-11(6H)-one 
• 118872-35-8 3-methyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridine 
• 118801-67-5 5,6,7,8-tetrahydro-1,2,4-triazolo<4,3-a>pyridin-3(2H)-one 
• 58156-38-0 9a-methoxy-2-methyl-7,8,9,9a-tetrahydro-6H-pyrido[2,1-b][1,3]oxazin-4-one 
• 61586-97-8 2,4-di-furan-2-yl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine 
• 61586-98-9 2,4-di-thiophen-2-yl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine 
• 70912-53-7 2,2-dimethyl-5-(piperidin-2-ylidene)-1,3-dioxane-4,6-dione 
• 53751-13-6 6-methoxy-5-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-2,3,4,5-tetrahydro-pyridine 
• 96600-80-5 4-amino-6,7,8,9-tetrahydroquinolizin-2-one 

Relevant academic research and scientific papers

The synthesis of 3-diazo-2-nitromethylenepiperidine

The synthesis of 3-diazo-2-nitromethylenepiperidine, in six steps from 2-piperidone, is reported. This is the first compound described which contains the 3-diazo-1-nitropropene function. The title compound is stable enough to be isolated and characterised in gram quantities using standard organic chemistry techniques and was used to prepare some 5-aza-spiro[2.5]octane and 4,5,6,7-tetrahydro-1H-pyrazolo-[4,3-b]pyridine derivatives.

Synthetic studies on the ceveratrum alkaloid skeleton

1-(2-Cyclohexenyl-1-carbonyl)-piperidine-2-carboxyaldehyde oxime (23) was prepared in 5 steps from pyridine-2-carboxaldehyde. Oxidation with NaOCl afforded the corresponding nitrile oxide which cyclized to give a 1:1 ratio of diastereomers 2aα,3,4,5,5aα,9,10,11aβ,11cα-decahydro-6H,8H-[1,2]benzisoxazolo[3, 4-ab]quinolizin-6-one (24A) and 2aα,3,4,5,5aα,9,10,11aα,11cα-decahydro-6H,8H-[1,2]benzisoxazolo[3, 4-ab]quinolizin-6-one (24B) in a best yield of 30%.

Sulfinate and Carbene Co-catalyzed Rauhut–Currier Reaction for Enantioselective Access to Azepino[1,2-a]indoles

A carbene and sulfinate co-catalyzed intermolecular Rauhut–Currier reaction between enals and nitrovinyl indoles is disclosed. The carbene catalyst activates the enal and the sulfinate co-catalyst activates the nitrovinyl indole. Both activation processes are realized via the formation of covalent bonds between the catalysts and substrates to generate catalyst-bound intermediates. The dual catalytic reaction affords azepino[1,2-a]indole products with excellent stereoselectivity. Our study demonstrates the unique involvement of sulfinate as an effective nucleophilic catalyst in activating electron-deficient alkenes for asymmetric reactions. This dual catalytic approach should also encourage future explorations of both sulfinate and carbene catalysts for new reactions.

FUSED BICYCLIC COMPOUNDS AND USES THEREOF IN MEDICINE

Fused bicyclic compounds and uses thereof in medicine. In particular, provided are fused bicyclic compounds used as ASK1 active regulator and and use of the compounds in the manufacture of a drug for treating a disease regulated by ASK1. Further provided are a pharmaceutical composition and a method of treating a disease regulated by ASK1 comprising administering the compounds or pharmaceutical composition thereof.

Dihydro pyridine compound, its composition, preparation method and use

Disclosed dihydropyridine compounds are the compounds possessing the following general formula (I) as shown in the specification, wherein R1 is selected from hydrogen, halogen, alkyl, substituted alkyl, alkoxy, substituted alkoxy, alkylamino, substituted alkylamino, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic groups, substituted heterocyclic groups, ester group and amide group; R2 is selected from hydrogen, cyanogroup, alkyl, substituted alky, alkenyl, substituted alkenyl and acyl; or R2 and R3 form a fused ring; R3 is selected from alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl; or R3 and R2 or R4 form a fused ring; R4 is selected from hydrogen, alkyl and substituted alkyl; or R4 and R3 or R5 form a fused ring; R5 is selected form alkyl, substituted alky, aryl, substituted aryl, heteroaryl and substituted heteroaryl; or R5 and R4 form a fused ring. The invention also discloses a preparation method of the compounds of the general formula (I), compositions containing the compounds of the general formula (I), and applications of the compositions to medicaments for treating cancers.

Synthesis of [1,2-A]-fused tricyclic dihydroquinolines by palladiumcatalyzed intramolecular C-N cross-coupling of polarized heterocyclic enamines

A simple methodology for [1,2-A]-fused tricyclic dihydroquinolines is established. The key ste of the methodology is an intramolecular Buchwald-Hartwig amination reaction of suitabl halogenated (both bromo and chloro) cyclic enaminoketones, enaminoesters and enaminonitrile with various ring size (from five-to seven-membered). Optimal reaction conditions (palladiu source, base, ligand) depend on the ring size of the starting enamine, giving 65-98% yield of th tricyclic product. A treatment of the products with perchloric acid gives respective quinoliniu perchlorates.

Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)

Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

Easily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetrafluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium salts is suggested. A partial drawback is the possibility of the formation of a mixture of products when using a different diazonium salt in each step due to a reversibility of the azo coupling. This can be suppressed by using a more reactive diazonium salt before a less reactive one.

Highly β-regioselective Friedel-Crafts aminoalkylation of pyrroles with cyclic perfluoroalkylated imines

A Friedel-Crafts-type alkylation reaction was studied between various pyrroles and α-polyfluoroalkylated cyclic imines that were activated by Lewis acids. The reaction proceeded under mild conditions and provided a high yielding synthesis of α-CF3-substituted pyrrolidines and piperidines as well as seven-membered analogues that contained a pyrrole ring. The unpredictably high β-selectivity for the aminoalkylation of both 1H-pyrrole and N-substituted pyrrole was observed as a result of a thermodynamically-controlled electrophilic substitution reaction. The computational data are in full agreement with the experimental results, which confirmed the observed regioselectivity as a result of the lower energy of the β-substituted pyrroles that contain α-trifluoromethyl-substituted pyrrolidine, piperidine, and azepane rings. Trifluoromethyl-substituted cyclic imines were activated by various Lewis acids and underwent a reaction with pyrrole derivatives. An unpredictable β-selectivity was observed. The regioselectivity of the aminoalkylation was explained by computation data, which also confirmed the isomerization of the α isomer into the β isomer. Copyright

SUBSTITUTED IMIDAZOHETEROCYCLE DERIVATIVES

The present invention provides substituted imidazoheterocycles having the general structure of formula (I), wherein Y is chosen from -O-, -OCRgRh-, -CRgRhO-, -CRgRh-, -(CRgRh)2-, -NRi-, -CRgRhNRi- and -NRiCRgRh-. Also provided are pharmaceutically acceptable salts, acid salts, hydrates, solvates and stereoisomers of the compounds of formula I. The compounds are useful as modulators of cannabinoid receptors and for the prophylaxis and treatment of cannabinoid receptor-associated diseases and conditions, such as pain, inflammation and pruritis.