Conventional and microwave assisted synthesis of pyrazolone Mannich bases possessing anti-inflammatory, analgesic, ulcerogenic effect and antimicrobial properties

In this study, ten 3-substituted indole derivatives at the 3rd position of indole nucleus were synthesized via Mannich reaction with microwave assisted synthesis and the conventional reflux heating method. Microwave assisted synthesis is more preferrable than reflux method since the microwave irradiation lead to a higher product yields with better purity and improved energy efficiency with shortened reaction time. The structures of 3-substituted indole derivatives were characterized by FT-IR, elemental analysis, 1H NMR and 13C NMR spectroscopy

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Microwave-assisted synthesis and anti-inflammatory activity evaluation of some novel α-aminophosphonates

Phosphorus Sulfur and Silicon and the Related Elements ◽

10.1080/10426507.2017.1331233 ◽

2017 ◽

Vol 192 (10) ◽

pp. 1110-1113 ◽

Cited By ~ 6

Author(s):

B. Sujatha ◽

S. Mohan ◽

Ch. Subramanyam ◽

K. Prasada Rao

Keyword(s):

Inflammatory Activity ◽

Microwave Assisted Synthesis ◽

Microwave Assisted ◽

Activity Evaluation ◽

Anti Inflammatory

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Microwave-Assisted Synthesis of Mono- and Disubstituted 4-Hydroxyacetophenone Derivatives via Mannich Reaction: Synthesis, XRD and HS-Analysis

Molecules ◽

10.3390/molecules24030590 ◽

2019 ◽

Vol 24 (3) ◽

pp. 590 ◽

Cited By ~ 5

Author(s):

Ghadah Aljohani ◽

Musa Said ◽

Dieter Lentz ◽

Norazah Basar ◽

Arwa Albar ◽

...

Keyword(s):

Hydrogen Bonding ◽

Intramolecular Hydrogen Bonding ◽

Chair Conformation ◽

Mannich Bases ◽

Secondary Amines ◽

Microwave Assisted Synthesis ◽

Microwave Assisted ◽

Regioselective Substitution ◽

Intramolecular Hydrogen ◽

Methyl Phenyl

An efficient microwave-assisted one-step synthetic route toward Mannich bases is developed from 4-hydroxyacetophenone and different secondary amines in quantitative yields, via a regioselective substitution reaction. The reaction takes a short time and is non-catalyzed and reproducible on a gram scale. The environmentally benign methodology provides a novel alternative, to the conventional methodologies, for the synthesis of mono- and disubstituted Mannich bases of 4-hydroxyacetophenone. All compounds were well-characterized by FT-IR, 1H NMR, 13C NMR, and mass spectrometry. The structures of 1-{4-hydroxy-3-[(morpholin-4-yl)methyl]phenyl}ethan-1-one (2a) and 1-{4-hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}ethan-1-one (3a) were determined by single crystal X-ray crystallography. Compound 2a and 3a crystallize in monoclinic, P21/n, and orthorhombic, Pbca, respectively. The most characteristic features of the molecular structure of 2a is that the morpholine fragment adopts a chair conformation with strong intramolecular hydrogen bonding. Compound 3a exhibits intermolecular hydrogen bonding, too. Furthermore, the computed Hirshfeld surface analysis confirms H-bonds and π–π stack interactions obtained by XRD packing analyses.

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