- Direct Synthesis of N,N-Dimethylated and β-Methyl N,N-Dimethylated amines from nitriles using methanol: Experimental and computational studies
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Direct and selective synthesis of N,N-dimethylated amines from nitriles using methanol as C1 building blocks is reported using an air- and moisture-stable ruthenium complex. Following this process, various aromatic as well as aliphatic nitriles were converted to the corresponding N-methylated amines. Interestingly, tandem C-methylation as well as N-methylation was achieved by introducing multiple methyl groups. The practical aspect of this process was revealed by preparative-scale reactions with different nitriles and the synthesis of anti-allergic drug "avil". Several kinetic experiments and detailed DFT calculations were carried out to understand the mechanism of this process.
- Paul, Bhaskar,Shee, Sujan,Panja, Dibyajyoti,Chakrabarti, Kaushik,Kundu, Sabuj
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p. 2890 - 2896
(2018/04/14)
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- Lewis Acid-Catalyzed Reductive Amination of Aldehydes and Ketones with N,N-Dimethylformamide as Dimethylamino Source, Reductant and Solvent
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A practical zinc acetate dihydrate-catalyzed reductive amination of various carbonyl compounds with N,N-dimethylformamide (DMF) as dimethylamino (Me2N) source, reductant and solvent has been developed. This reaction shows broad substrate scope,
- Yang, Luo,Lin, Jie,Kang, Lei,Zhou, Wang,Ma, Da-You
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supporting information
p. 485 - 490
(2018/01/15)
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- Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines
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A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)2/NIXANTPHOS-b
- Kim, Byeong-Seon,Jiménez, Jacqueline,Gao, Feng,Walsh, Patrick J.
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supporting information
p. 5788 - 5791
(2015/12/11)
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- Homoazanicotine: A structure-affinity study for nicotinic acetylcholine (nACH) receptor binding
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We have recently identified 3-[(1-methyl)-4,5-dihydro-1H-imidazol-2-yl)methyl]pyridine (homoazanicotine, 8) as a novel nicotinic acetylcholinergic (nACh) receptor ligand. In the present investigation, after we determined that 8 binds selectively at nicoti
- Ferretti,Dukat,Giannella,Piergentili,Pigini,Quaglia,Damaj,Martin,Glennon
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p. 4724 - 4731
(2007/10/03)
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- Reaction of Pyridine and Picolines N-oxides with Hexamethylphosphoroamide. New Way to Dimethylamino Derivatives of Azaaromatic Compounds
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The reaction of pyridine, 2-, 3-, and 4-picoline N-oxides with hexamethylphosphoramide (HMPA) was studied in the temperature range of 150-230 deg C with and without polyphosphoric acid (PPA) as catalyst. Pyridine and 3-picoline N-oxides gave their 2-dimethylamino derivatives as well as deoxygenation products. In the case of 2- and 4-picoline N-oxides 2- and 4-dimethylaminomethylpyridines were formed, respectively as well as 2- and 4-picoline. Key words: hexamethylphosphoramide, pyridine and picoline N-oxides, 2-dimethylaminopyridine, 2- and 4- dimethylaminomethylpyridines
- Czuba, W.,Wodzinska, J.
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p. 1343 - 1346
(2007/10/02)
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- Remote controlled nucleophilicity, 2: Lithiated C(α)-substituted 4-methylpyridines
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C(α)-substituted 4-methylpyridines have been N-lithiated and reacted with chlorotrimethylsilane and other electrophiles. The lithiated C(α)-NMe2 substituted intermediate shows an interesting dichotomy of behavior towards electrophiles: It represents the borderline between compounds for which an extreme N or C(α) regionucleophilicity is observed.
- Anders,Opitz,Bauer
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p. 1221 - 1227
(2007/10/02)
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