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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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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

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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

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Ring Chain Transformations. XIV. 3-(omega-Aminoalkyl)-1,2,4-triazoles by Reaction of Isothiosemicarbazides with Lactam Acetals or Lactim Ethers

Isothiosemicarbazide hydrohalides 1 react with lactam acetals 2 or lactim ethers 3 by the formation of lactamisothiosemicarbazones 4 or ring transformed 3-(omega-aminoalkyl)-1,2,4-triazoles 6.The latter can independently by synthesized by alkylation of lactamthiosemicarbazones 9.Condensation of primary 3-(omega-aminoalkyl)-1,2,4-triazoles 6 with lactim ethers 7 can lead to 3-lactamiminoalkyl-1,2,4-triazoles 8.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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Cyclic amidine analogues of taurine and homotaurine: Synthesis and effects on rat skeletal muscle

A series of amidinosulfonic acids IIIa-f, analogs of taurine and homotaurine, was synthesized by reacting 2-aminoethane or 3-aminopropane sulfonic acid with lactim ethers Ia-c and then cyclized to sultams IVa-c and Vd-f. The effects of some selected amidinosulfonic acids III on membrane ionic conductances of rat skeletal muscle are described.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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A Novel Class of “GABAergic” Agents: 1-Aryl-3-(aminoalkylidene)oxindoles

Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles.Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)ethylidene and N-methyl-2-pyrrolidinylidene side chains.The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels.Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid.Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Chemistry is traditionally divided into organic and inorganic chemistry. category: pyrrolines, The former is the study of compounds containing at least one carbon-hydrogen bonds.In a patent£¬Which mentioned a new discovery about 5264-35-7

1-Aza-2-azoniaallene salts: Reactions with azomethines and other N-nucleophiles

Azomethines undergo nucleophilic addition to 1-aza-2-azoniaallene salts 7 to furnish N-(azoalkyl)iminium salts (e.g. 10, 12, 13). With cyclic hydrazones such as pyrazole or indazole, heterocumulenes 7 afford bicyclic 1,2,4,5-tetrazinium salts (e.g. 14, 16), or simple N-adducts such as 15, 17. On the other hand, with open-chain hydrazones azinium salts 19 are formed. Benzotriazole and the aziridine 21 react with 1-aza-2-azoniaallene salts 7 to afford (azoalkyl)ammonium salts 20, 22. The heterocumulenes 7 undergo cycloaddition across the C=N double bond of the azirine 23 to furnish azirenotriazolium salts 25, while with the 1-aza-2-azoniaallene salt 3a the triazolium salt 28 was formed. The constitutions of compounds 22, 25a and 28 were confirmed by X-ray structural analyses.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem