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2,6-dimethoxyphenyl-substituted n-heterocyclic carbenes (NHCs): A family of highly electron-rich organocatalysts

Based on our recent finding that 2,6-dimethoxyphenyl-substituted NHCs show superior reactivity in the hydroacylation reactions of electron-neutral olefins compared with known NHCs, we now report the syntheses and crystal structures of four highly electron-rich 2,6-dimethoxyphenyl-substituted NHCs and show the increase in efficiency caused by the electron-rich aryl substituent in hydroacylation reactions. The synthesis and crystal structures of four highly electron-rich 2,6-dimethoxyphenyl-substituted NHCs are reported. These NHCs should have interesting applications as ligands or in NHC organocatalysis.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Tertiary amines

Tertiary amines of the formula STR1 wherein A1, A2, A3, A4, L, M, p, T, and Q are as defined herein, have antimycotic and cholesterol-lowering activity.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Substituted ureas and processes for their preparation

Organic chemical compounds based upon the urea molecule are disclosed which have potent gastric secretion inhibitory properties. The urea is substituted with a heterocyclic ring which may be substituted with one or more loweralkyl groups. The urea is also substituted with loweralkyl and a lower-alkylamino loweralkyl group. The compounds have profound effects on the inhibition of gastric secretions in the gastro-intestinal tract, and compositions for such uses are also disclosed.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Reaction of lactim ethers and lactim sulfides with electrophiles: Attack at nitrogen followed by ring-opening under neutral conditions

Electrophilic push-pull molecules react at the nitrogen of lactim ethers and lactim sulfides; subsequent hydrolysis gives ring-opened products in good yields.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Chemical and computational methods for the characterization of covalent reactive groups for the prospective design of irreversible inhibitors

Interest in drugs that covalently modify their target is driven by the desire for enhanced efficacy that can result from the silencing of enzymatic activity until protein resynthesis can occur, along with the potential for increased selectivity by targeting uniquely positioned nucleophilic residues in the protein. However, covalent approaches carry additional risk for toxicities or hypersensitivity reactions that can result from covalent modification of unintended targets. Here we describe methods for measuring the reactivity of covalent reactive groups (CRGs) with a biologically relevant nucleophile, glutathione (GSH), along with kinetic data for a broad array of electrophiles. We also describe a computational method for predicting electrophilic reactivity, which taken together can be applied to the prospective design of thiol-reactive covalent inhibitors.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Lactim ethers in the synthesis of 1,2-polymethylene-4-quinazolones

Condensation of lactim ethers with amides of o-halogeno-substituted aromatic acids was investigated. Derivatives of 5,7,8,9,10,11-hexahydroazepino[1,2-a]quinazolin-5-one and 1,2,3,4-tetrahydropyrrolo-[1,2-a]quinazolin-5-one were obtained.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

More research is needed about 5-Methoxy-3,4-dihydro-2H-pyrrole

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PYRROLIDINOHYDROCHINAZOLINES

Disclosed are compounds of formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, wherein the groups Ar1, Ar2, A, R1, R2, R3, E1, E2, X and n are as defined in the description and claims, which are effective modulators of chemokine activity.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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PMR SPECTRA AND cis-trans ISOMERISM OF 2-METHYLENEPYRROLIDINE AND 2-METHYLENETETRAHYDROFURAN DERIVATIVES

A number of secondary enamines and cyclic enol ethers (2-methylenetetrahydrofuran derivatives) were synthesized by the reaction of O-methylbutyrolactim and 2,2-diethoxytetrahydrofuran, respectively, with compounds that have an active methylene link.The absence of reversible cis-trans isomerization was established in a study of the PMR spectra of these compounds.The configuration of the secondary enamines is determined by the possibility of the formation of a strong intramolecular hydrogen bond between the carbonyl-containing substituent and the NH group.In the case of the cyclic enol ethers it was shown that the energy barrier to cis-trans isomerization is greater than 25 kcal/mole and that, as a consequence of this, the geometrical isomers can be separated preparatively.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Ruthenium catalyzed decarbonylative arylation at sp3 carbon centers in pyrrolidine and piperidine heterocycles

This paper describes the development of a new catalytic transformation, the ruthenium-catalyzed decarbonylative arylation of cyclic 2-amino esters, which replaces the ester group with an aryl ring at the sp3 carbon center. For example, proline ester amidine 1 is converted to 2-arylpyrrolidine 3 in the presence of arylboronic acids or esters as arene donors and Ru 3(CO)12 as the catalyst. This process provides a rapid access to a variety of 2-arylpyrrolidines and piperidines from commercially available proline, hydroxyproline, and pipecolinate esters. The examination of the substrate scope also showed that many arene boronic acids and boronate esters serve as coupling partners. The high chemoselectivity of this process was demonstrated and ascribed to the significant rate difference between the decarbonylative arylation and the C-H arylation. The decarbonylative arylation complements the C-H arylation, since the latter process lacks control over the extent of functionalization, affording a mixture of mono- and bis-arylpyrrolidines. When applied in tandem, these two processes provide 2,5-diarylpyrrolidines in two steps from the corresponding proline esters. It was also demonstrated that the required amidine or iminocarbamate directing group fulfills two major functions: first, it is essential for the ester activation step, which occurs via the coordination-assisted metal insertion into the acyl C-O bond; second, it facilitates the decarbonylation, via the stabilization of a metallacycle intermediate, assuring the formation of the 2-arylated products instead of the corresponding ketones observed before by others.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Acetals of lactams and acid amides. 35. Synthesis of condensed two- and three-ring pyridine systems on the basis of enamino amides

The synthesis of 2,3,5,6-tetrahydropyrrolo[3,2-c]pyrid-6-one was accomplished by rearrangement of 8H,1-cyano-8-dimethylaminomethylene-2,5,6,7-tetrahydropyrrolo[1, 2-c]pyrimidine. Pyrrolo[3,2-c]pyrimidine, 1,6-naphthyridine, and pyrimido[4,3-b]-azepine derivatives were synthesized on the basis of enamino dinitriles. The hydrolysis of 8H,1-cyano-8-dimethylaminomethylene-2,5,6,7-tetrahydropyrrolo[1,2-c]-pyrimidine in 50% CH3COOH leads to a pyrrolo[1,2-c]pyrido[4?,3?-d]pyrimidine derivative. A similar dipyrido[4,3-d-1?,2?-c]pyrimidine derivative was obtained from 1-cyano-9-dimethylaminomethylene-2,5,6,7,8,9-hexahydropyrido[1,2-c]pyrimidine under these conditions, and 3,4-dioxo-3,4,7,8,9,10-hexahydropyrido[1,2-c]pyrano[4?,3?-d]-pyrimidine was synthesized bytreatment with a 1 N solution of HCl.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem