This paper deals with the synthesis of some novel 1,4-Dihydropyride derivatives derivatives. The 1,4-Dicyanopyride (DHPM ) derivatives have been synthesized through novel synthetic process.
The synthesized compound was well characterized by IR, 1H NMR and 13C NMR, Mass spectrometry. To know the absolute configuration of the synthesized compounds, X-Ray crystallography study was also performed by developing the crystal of the compounds.
Table of Contents
1 Introduction
1.1 Experimental
1.2 Spectral Discussion
1.3 X-ray Diffraction Data
1.4 Experimental Details
1.5 Crystal Structure Images
1.6 Packing diagram of the molecules when viewed down the b axis.
1.7 Representative spectrums
1.8 References
Objective and Research Focus
This work focuses on the synthesis, structural characterization, and single-crystal X-ray diffraction analysis of the novel 1,4-dihydropyridine derivative 4-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile. The primary objective is to elucidate the molecular and crystal structure of this specific compound, which belongs to a class of heterocycles with significant potential in pharmacological applications such as multi-drug resistance reversal and antihypertensive therapy.
- Synthesis of a novel dicyano-substituted 1,4-dihydropyridine derivative.
- Comprehensive spectral characterization using IR, 1H NMR, 13C NMR, and Mass Spectrometry.
- Determination of the three-dimensional molecular geometry via single-crystal X-ray diffraction.
- Analysis of crystal packing, bond lengths, angles, and torsion parameters.
Excerpt from the Book
1.1.3 Preparation of (3-methoxy-4-(prop-2-yn-1yloxy)phenyl)-2,6-dimethyl-1,4dihydropyridine-3,5-dicarbonitrile
The present work, reports synthesis and crystal structure of 4-(3-methoxy-4-(prop-2-yn-1yloxy)phenyl)-2,6-dimethyl 1,4dihydropyridine-3,5-dicarbonitrile (3) studied in this work was synthesized from a 3-methoxy-4-(prop-2-yn-1 yloxy) benzaldehyde (1) with (Z)-3-aminobut-2-enenitrile in glacial acetic acid solvent at 60 °C for 30 minute. Reaction was completed as monitored by TLC, the reaction product was filtered to obtain crude product. The precipitate was filtered and recrystallized with ethanol to get pure product. The physical and spectral data of compound are as follow: colorless crystal, yield 90% ; m.p. 180-182 °C.
Summary of Chapters
1 Introduction: Provides an overview of the importance of 1,4-dihydropyridine derivatives in medicinal chemistry and outlines the research context for dicyano-substituted derivatives.
1.1 Experimental: Describes the general analysis protocols, including apparatus for melting point determination, spectroscopic methods, and chromatography.
1.2 Spectral Discussion: Details the interpretation of IR, Mass, 1H NMR, and 13C NMR spectra to confirm the molecular structure of the synthesized compound.
1.3 X-ray Diffraction Data: Presents the crystallographic data collection, structure solution methods, and refinement parameters for the colorless block crystal.
1.4 Experimental Details: Tabulates the precise crystal data, intensity measurements, and refinement statistics.
1.5 Crystal Structure Images: Displays the ORTEP diagram illustrating the molecular structure with 50% probability thermal ellipsoids.
1.6 Packing diagram of the molecules when viewed down the b axis.: Provides a visual representation of how the molecules are arranged within the crystal lattice.
1.7 Representative spectrums: Includes the full graphical data for the IR, Mass, 1H NMR, and 13C NMR analyses.
1.8 References: Lists the scientific literature and software documentation used to support the research methodology and findings.
Keywords
1,4-Dihydropyridine, Dicyano-substitution, Crystal Structure, X-ray Diffraction, Spectroscopy, Synthesis, Heterocycles, Molecular Geometry, Triclinic System, Bond Lengths, Bond Angles, Medicinal Chemistry, NMR Analysis, IR Spectroscopy, Crystallography.
Frequently Asked Questions
What is the core subject of this research paper?
The paper focuses on the synthesis and the structural characterization of a specific dicyano-substituted 1,4-dihydropyridine derivative, particularly its single-crystal structure.
What are the primary fields of application for the synthesized compounds?
These compounds are known for their potential in medicinal chemistry, specifically as calcium channel blockers and for multi-drug resistance reversal in tumor cells.
What is the research goal of this document?
The goal is to report the successful synthesis of the target molecule and to provide a high-resolution 3D structural model verified by X-ray crystallography.
Which scientific methods are utilized for structural verification?
The authors utilized a combination of spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, and Mass Spectrometry) alongside X-ray diffraction analysis for definitive structural proof.
What does the main body cover?
It covers the synthesis protocol, the spectral data analysis, the methodology used for crystal data collection, and detailed tables regarding atomic coordinates, bond lengths, and angles.
What keywords characterize this study?
Key terms include 1,4-dihydropyridine, X-ray diffraction, crystal structure, synthesis, and various spectroscopic methodologies.
In what crystal system does the synthesized compound crystallize?
The compound crystallizes in the triclinic crystal system with space group P-1.
What was the reported yield and melting point of the compound?
The synthesis resulted in a 90% yield of the compound, which displayed a melting point range of 180-182 °C.
Which specific software was used for the structure solution?
The structure was solved using Direct Methods (SIR92) and refined using the SHELXL-97 software package.
What is the significance of the packing diagram provided?
The packing diagram, viewed down the b axis, provides insight into the molecular arrangement and intermolecular interactions within the crystal lattice.
- Quote paper
- Krunalkumar R. Mehariya (Author), Bhagwati K. Gauni Mehariya (Author), 2010, Synthesis, Characterization, and Single Crystal Structure of 4-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile, Munich, GRIN Verlag, https://www.grin.com/document/321425
