Mannich Bases as Synthetic Intermediates: Alkylation of Amines and Diamines with Bis-ketonic Mannich Bases

2008 ◽  
Vol 63 (5) ◽  
pp. 577-584 ◽  
Author(s):  
Elsayed M. Afsah ◽  
Metwally Hammouda ◽  
Mona M. Khalifa ◽  
Essam H. Al-shahaby
Keyword(s):  
Mannich Base ◽  
Mannich Bases ◽  
Ring System ◽  
Methylamine Hydrochloride ◽  
Synthetic Intermediates

The bis-ketonic Mannich base, N,N-bis(β -benzoylethyl)methylamine hydrochloride (1) reacts with primary arylamines and diamines to give ketonic sec-arylamines 3a - e and 4. The piperidines 7a - c were obtained from 1 and primary alkylamines, whereas the 1,4-diazepine derivative 10 was obtained from 1 and ethylenediamine. Treatment of the bis-base 1,4-di[β -(N-morpholino)propionyl]benzene bis(hydrochloride) (11) with primary arylamines gave the corresponding bis-(sec-arylamines) 12a - b, whereas its reaction with ophenylenediamine afforded the bis[1,5-benzodiazepine] ring system 14. The synthesis of the diazacyclophane ring system 15 has been achieved by treating 11 with piperazine. Attempted synthesis of 4- aza-[7]-paracyclophane (16) from 11 and benzylamine led to 17. The reaction of 1 or 11 with phenylhydrazine gave the 2-pyrazolines 18 and 19. Treatment of 3 or 4 with phenylhydrazine and formaldehyde afforded the 2H-1,2,4-triazepines 20a - c and the bis[2H-1,2,4-triazepine] ring system 21.

scholarly journals Synthesis, Characterization and Biological Evaluation of 1, 2-Disubstituted Benzimidazole Derivatives using Mannich Bases

2010 ◽  
Vol 7 (1) ◽  
pp. 222-226 ◽  
Author(s):  
B. Anil Reddy
Keyword(s):  
Spectral Data ◽  
Carboxylic Acids ◽  
Benzene Ring ◽  
Mannich Base ◽  
Mannich Bases ◽  
Biological Evaluation ◽  
Ring System ◽  
Inflammatory Activity ◽  
Benzimidazole Derivatives ◽  
Benzimidazole Ring

The ring system in which a benzene ring is fused to the 4,5-positions of imidazole is designated as benzimidazole. Condensations of 2-substituted benzimidazole derivatives were synthesized by different carboxylic acids using Mannich base and anti-inflammatory activity. The various positions on the benzimidazole ring are numbered in the manner indicated with the imino function as number one. The formations of the product were conformed by the analytical and spectral data.

scholarly journals Reaction of Thiols with formaldehyde in Presnce of succinimid and Reduction of Phenyl Tetrazole Derivative with Hydrogen and Borohydraide

2011 ◽  
Vol 8 (2) ◽  
pp. 388-393
Author(s):  
Baghdad Science Journal
Keyword(s):  
Mannich Base ◽  
Mannich Bases ◽  
Hydrogen Gas ◽  
Equimolar Amount ◽  
Methanol Solution ◽  
Biologically Active ◽  
Wide Field ◽  
Tetrazole Derivative ◽  
Potassium Borohydride ◽  
Palladium On Carbon

One of most the important compounds which have active hydrogen (substrate) is the thiols which used in a wide field in preparation of Mannich bases . A large number of Mannich bases have been prepared as a biologically active compound (pharmaceutical, pesticides, bactericidal, fungicidal and tuberculostatic) and in order to correlate their structure and reactivity with their pharmacological activity such as . It has been reported that the reaction is easily proceeded by using primary and secondary amine beside formaldehyde. But when we tried the reaction of thiols as substrate and formaldehyde and succinimide instead of amine, the reaction did not proceed to give Mannich base but product were methylenene – bis – sulfide . Mannich base can go farther reaction such as (addition, substitution, cleavge, polymerization, hydrogenation) to produce numerous numberbof compound so we tried to hydrogenation tetrazole derivative which gave different product which depened on type of hydrogen on reagent. Reduction of 2 – ethyl benzoyle – phenyl tetrazole which performed with hydrogen gas in methanol solution in presence palladium on carbon as catalyst, the tow products were separated by column chromatography. Reduction of 2 – methyl – 2 (2 – cycloheptane) – 5- phenyl tetrazole. The methanolic solution the ketone was refluxed with equimolar amount of potassium borohydride and the product is isolated and purified to give. and identified by C.H.N analysis and NMR spectra.

scholarly journals Resistance against Membrane-Inserting MmpL3 Inhibitor through Upregulation of MmpL5 in Mycobacterium tuberculosis

2020 ◽  
Vol 64 (12) ◽  
Author(s):  
Ming Li ◽  
Samuel Agyei Nyantakyi ◽  
Mei-Lin Go ◽  
Thomas Dick
Keyword(s):  
Antibacterial Activity ◽  
Mycobacterium Tuberculosis ◽  
Mouse Model ◽  
Mannich Base ◽  
Efflux Pump ◽  
Transcriptional Repressor ◽  
Mannich Bases ◽  
Mycolic Acid ◽  
Low Level ◽  
Level Resistance

ABSTRACT Spiroketal indolyl Mannich bases (SIMBs) present a novel class of membrane-inserting antimycobacterials with efficacy in a tuberculosis mouse model. SIMBs exert their antibacterial activity by two mechanisms. The indolyl Mannich base scaffold causes permeabilization of bacteria, and the spiroketal moiety contributes to inhibition of the mycolic acid transporter MmpL3. Here, we show that low-level resistance to SIMBs arises by mutations in the transcriptional repressor MmpR5, resulting in upregulation of the efflux pump MmpL5.

scholarly journals Synthesis, Characterization & Antimicrobial Activities of New Isoxazole Substituted Mannich and Schiff Bases of 5-Nitroisatin Analogs

2020 ◽  
Vol 32 (4) ◽  
pp. 970-974
Author(s):  
Ch. Jithendra ◽  
G. Saravanan ◽  
V. Alagarsamy ◽  
T. Panneerselvam ◽  
K. Selvaraj ◽  
...  
Keyword(s):  
Biological Activity ◽  
Functional Group ◽  
Mannich Base ◽  
Antimicrobial Activities ◽  
Mannich Bases ◽  
Pathogenic Microorganism ◽  
Diffusion Technique ◽  
Group Variation ◽  
The Relationship ◽  
Isoxazole Derivatives

A sequence of new isoxazole substituted Schiff base and Mannich base of 5-nitroisatin are synthesized by a multi-step synthesis from 5-nitroisatin. Whole synthesized analogs were characterized using IR, NMR, Mass spectroscopy and microanalyses. All the Schiff and Mannich bases were tested for their antimicrobial potencies against some human pathogenic microorganism using agar well diffusion technique. The relationship between the biological activity and the functional group variation of the Schiff and Mannich bases were analyzed. Standard ciprofloxacin and ketoconazole were used to compare the antimicrobial activities of novel isatin coupled isoxazole derivatives.

Oxygen atom transfer between DMSO and benzoin catalyzed by cis-dioxidomolybdenum(vi) complexes of tetradentate Mannich bases

2018 ◽  
Vol 42 (8) ◽  
pp. 6225-6235 ◽  
Author(s):  
Mannar R. Maurya ◽  
Bekele Mengesha ◽  
Bhawna Uprety ◽  
Nancy Jangra ◽  
Reshu Tomar ◽  
...  
Keyword(s):  
Oxygen Atom ◽  
Mannich Base ◽  
Mannich Bases ◽  
Atom Transfer ◽  
Oxygen Atom Transfer

Dioxidomolybdenum(vi) complexes of tetradentate ONNO donor Mannich base ligands for the catalytic oxygen atom transfer between benzoin and DMSO are reported.

α-Dicarbonylmonohydrazone und ihre Acylderivate als Nucleophile und Nachbargruppen/α-Dicarbonylmonohydrazones and their Acylderivatives as Nucleophiles and Neighbouring Groups

2003 ◽  
Vol 58 (9) ◽  
pp. 885-902 ◽  
Author(s):  
Hans Möhrle ◽  
Georg Keller
Keyword(s):  
Perchloric Acid ◽  
Mannich Base ◽  
Mannich Bases ◽  
Aminomethyl Derivatives

The aminomethylation of the α-carbonylhydrazones 1 and 14 with N,N,N′,N′-tetralkylaminals yields only N,N- or C,N-bis-aminomethyl products, but no C-mono-aminomethyl compounds. Phenylglyoxal N-methylhydrazone (24) yields the Mannich bases 27, while anilinocarbonyl hydrazone 29 dependent on the conditions gives rise to the N-aminomethyl derivatives 30 or to the Mannich bases 31. From benzoylhydrazone 33 and semicarbazone 35 the Mannich bases 34 and 36, respectively, are available. Mercury-EDTA reacts with 27 and 31 by twofold dehydrogenation and cyclization to form the lactams 46 and 47, respectively, whose treatment with perchloric acid yields the triazinium salts 45 and 51. When Mannich base 34 is exposed to the same oxidation conditions, the products of both dehydrogenation steps, 54 and 55, may be isolated. From the semicarbazones 36 only the triazines 56 are produced after a single dehydrogenation step.

Synthesis of some new mixed azines, Schiff and Mannich bases of pharmaceutical interest related to isatin

2015 ◽  
Vol 70 (6) ◽  
pp. 393-402 ◽  
Author(s):  
Elsayed M. Afsah ◽  
Saad S. Elmorsy ◽  
Soha M. Abdelmageed ◽  
Zaki E. Zaki
Keyword(s):  
Schiff Bases ◽  
Mannich Base ◽  
Mannich Bases ◽  
Pyromellitic Dianhydride

AbstractThe mixed azines 3a–h and 4 were obtained by treating 3-hydrazonoindolin-2-one (2) with the appropriate aldehyde or dialdehyde. Treatment of 3b or 3c with formaldehyde or glutaric dialdehyde and the appropriate amine afforded the azine Mannich bases 5–7. The condensation of isatin or its N-Mannich base 8 with 1-aminopiperidine, 4-aminomorpholine and 1,4-diaminopiperazine gave 10a–d, 12 and 13. The Mannich bases 14 and 15 were obtained from 10a and 10b. Treatment of 2 with succinic, phthalic and quinolinic anhydride and pyromellitic dianhydride afforded compounds 16, 17a, 17b and 18, respectively. The synthesis of isatin Schiff bases incorporating a benzoylpiperidine, benzoylmorpholine and 1,4-dibezoylpiperazine moiety and their N-Mannich bases was investigated.

Mannich Bases as Synthetic Intermediates: Synthesis of 3- and 4-Functionalized 2-Pyrazolines

2007 ◽  
Vol 62 (4) ◽  
pp. 540-548 ◽  
Author(s):  
Elsayed M. Afsah ◽  
Ez-el-Din M. Kandeel ◽  
Mona M. Khalifa ◽  
Waleed M. Hammouda
Keyword(s):  
Mannich Bases ◽  
Reaction Conditions ◽  
Synthetic Intermediates

The reaction of styryl ketonic Mannich bases 2a - c with phenylhydrazine leads to 3-functionalized 2-pyrazolines 4 or 6 depending on the reaction conditions. 3-[β -(Arylamino)ethyl]-2-pyrazolines 8a,b were obtained via transamination between the methiodide salt 7 and primary arylamines. Treatment of 1-(p-anisyl)-1,2,5-tri(N-piperidino)pentan-3-one (11) with phenylhydrazine affords the 3,4-difunctionalized 2-pyrazoline 12. The reactions of the keto bases 19 or 21 with hydrazines lead to 4-functionalized 2-pyrazolines 20 and 22, the N-Mannich bases 23 and 24 are obtained from 22a. The synthesis of 3-[β -(phenylthio)ethyl]-2-pyrazolines 28a,b has been achieved by treating 26 or 27 with phenylhydrazine.

scholarly journals SYNTHESIS, BIOLOGICAL STUDY, DNA INTERACTION OF MANNICH BASE METAL COMPLEXES DERIVED FROM BENZAMIDE

2021 ◽  
pp. 60-64
Author(s):  
SIVAKAMI SUDHASANKAR
Keyword(s):  
Metal Complexes ◽  
Mannich Base ◽  
Dna Interaction ◽  
Mannich Bases ◽  
Molar Conductance ◽  
Biological Study ◽  
Spectral Studies ◽  
Mass Spectral ◽  
Calf Thymus ◽  
Uv Visible

Objective: Coordination compounds occur widely in nature and they comprise a large share of current inorganic research. The Mannich reaction is a classic method for the preparation of Mannich bases, namely, β amino compounds, which are heterocyclic. Methods: A novel Mannich base of N-((3,4-dimethoxyphenyl)(2,5-dioxopyrrolidin-1-yl) methyl)benzamide and its coordination complexes with transition metals Mn and Co have been synthesized and characterized by elemental analysis, molar conductance, magnetic susceptibility measurements, UV-Visible, IR, NMR, and Mass spectral studies. Results: Based on the magnetic moment and UV-Visible spectral data, octahedral geometries were assigned for the metal complexes. The metal complexes were screened for antifungal activity. Conclusion: the metal complexes have shown good activity than the ligand. The binding of selected metal complexes with calf thymus DNA was investigated. It is found that the cobalt (II) metal complex of the ligand showed efficient DNA binding ability.

Chemistry of Phosphorus Ylides, 11

1991 ◽  
Vol 46 (8) ◽  
pp. 1105-1109 ◽  
Author(s):  
Fouad M. Soliman ◽  
Medhat M. Said
Keyword(s):  
Elemental Analysis ◽  
Mannich Base ◽  
Mannich Bases ◽  
The Other ◽  
Phosphorus Ylides ◽  
Other Hand ◽  
New Compounds

The reaction of 1-hydroxyxanthenone (1) and hydroxyquinoline (10, 13) Mannich bases with the reactive phosphacumulated ylides (2), represents a new way for the synthesis of the pyranones and pyranthiones (5, 11, 14). On the other hand, the stabilized phosphorus ylides (6) affect the transylidation of the Mannich base (1) to the corresponding phosphoranylidenes (9). The structure of the resulting new compounds has been confirmed through elemental analysis and spectroscopic results (IR, 1H, 31P NMR and MS).

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