2-Naphthol-pyrazole conjugates as substrates in the Mannich reaction

2018 ◽  
Vol 73 (5) ◽  
pp. 275-280
Author(s):  
Gheorghe Roman
Keyword(s):  
Methyl Iodide ◽  
Mannich Reaction ◽  
Benzyl Chloride ◽  
Pyrazole Ring ◽  
The Mannich Reaction ◽  
Chloride Methyl

AbstractSeveral novel 2-naphthol-pyrazole conjugates have been synthesized through the O-alkylation of 1-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]naphthalen-2-ol with methyl iodide, benzyl chloride, methyl bromoacetate and N-benzyl-2-bromoacetamide. The aminomethylation of these 2-naphthol-pyrazole conjugates has been examined employing the classical conditions for the Mannich reaction, and also by using N,N-dimethylmethyleneiminium chloride as preformed aminomethylating reagent. In both situations, aminomethylation of these substrates occurred at C-4 of the pyrazole ring. The bifunctional substrate 1-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]naphthalen-2-ol has been chemoselectively aminomethylated in the pyrazole ring using the same preformed aminomethylating reagent.

UNSYMMETRICALLY SUBSTITUTED 3,3′-METHYLENE BRIDGED 2,2′-DIHYDROXYCHROMONES

1958 ◽  
Vol 36 (11) ◽  
pp. 1501-1510 ◽  
Author(s):  
R. A. Abramovitch ◽  
J. R. Gear
Keyword(s):  
Methyl Iodide ◽  
Infrared Spectra ◽  
Mannich Reaction ◽  
Good Yield ◽  
Addition Reactions ◽  
Michael Type Addition ◽  
The Mannich Reaction

Unsymmetrically substituted dicoumarol derivatives have been synthesized by taking advantage of the fact that 4-hydroxycoumarins will undergo the Mannich reaction at C3 and also take part in Michael-type addition reactions. In the presence of methyl iodide, 4-hydroxy-3-N-piperidinomethylcoumarin and 4-hydroxycoumarin gave dicoumarol. By using monosubstituted 4-hydroxycoumarins a variety of unsymmetrically substituted dicoumarols have been prepared in good yield. The infrared spectra of some of the intermediates and products are reported and discussed.

The Mannich Reaction Between Aromatic Ketones, Aromatic Aldehydes and Aromatic Amines

Synthesis ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 717-718 ◽  
Author(s):  
Yi Lin ◽  
Lei Huangshu ◽  
Zou Junhua ◽  
Xu Xiujuan
Keyword(s):  
Mannich Reaction ◽  
Aromatic Amines ◽  
Aromatic Aldehydes ◽  
Aromatic Ketones ◽  
The Mannich Reaction

scholarly journals Studies on 1-Alkyl-2(1H)-pyridone Derivatives. XXI. The Mannich Reaction of 2-Methyl-1(2H)-thioisoquinolone

1974 ◽  
Vol 94 (1) ◽  
pp. 124-126 ◽  
Author(s):  
HIROSHI TOMISAWA ◽  
CHAO HSIUNG WANG ◽  
HIDEKI KATO
Keyword(s):  
Mannich Reaction ◽  
The Mannich Reaction

scholarly journals Synthesis Of 4-Alil-6- (Hydroxymethyl) -2-Methody Phenol Compounds from Eugenol Through Mannich Reaction Followed Methylation with Methyl Iodide and Subtitution Using NaOH

2019 ◽  
Vol 1 (1) ◽  
pp. 75-85
Author(s):  
Sabarmin Perangin-angin
Keyword(s):  
Nucleophilic Substitution ◽  
Methyl Iodide ◽  
Mannich Reaction ◽  
Substitution Reaction ◽  
Relative Molecular Mass ◽  
Hydroxymethyl Group ◽  
Phenol Compounds ◽  
Ms Analysis ◽  
Stretching Vibration ◽  
Solid Form

Eugenol derivative compound 4-allyl-6-hydroxymethyl-2-methoxy phenol was synthesized through Mannich reaction, methylation, dan nucleophilic substitution. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40 % in reflux condition with n-heptane solvent at temperature 98o-100oC for 10 hours produced 4-allyl-6-(dimethylamino)methyl-2-methoxy phenol with yield of 83 %. The formation of dimethylaminomethyl group supported by C-N stretching vibration at 1246,16 cm-1 and ion molecule peak at 221 in GC-MS analysis. Methylation of 4-allyl-6-(dimethylamino)methyl-2-methoxy phenol was carried out with methyl iodide in ethanol solvent produced 6-((N-iodo-N-methyl-N-methyl-N-methylamino) methyl)-4-allyl-2-methoxy phenol in solid form, which then purified by recrystallization with 78,15 % yield. 4-allyl-6-(hydroxymethyl)-2-methoxy phenol was synthesized by nucleophilic substitution reaction of 6-((N-iodo-N-methyl-N-methyl-N-methylamino)methyl)-4-allyl-2-methoxy phenol with sodium hydroxide in reflux condition then purified by coloum chromatography gave liquid compound with yield of 65,05%. The formation of hydroxymethyl group supported by OH vibration at 3433,9 cm-1 and ion molecule peak at 194 in GC-MS analysis show the relative molecular mass of synthesized product.

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