Targeted Intermediates of Eudesmic Acid: Synthesis and X

It was carried out synthesis of esters and their dinitro derivatives of 3,4,5-trimethoxybenzoic (eudesmic) acid. Esterification of eudesmic acid carried out n absolute methanol or ethanol and corresponding methyl and ethyl 3,4,5-trimethoxybenzoates ( have been synthesized in good yields. It was revealed that nitration of these esters gives only dinitro products. The structure of the synthesized compounds of the methyl and ethyl 2,6 trimethoxybenzoates (4, 5) was determined by X diffraction analysis (XRD). In the asymmetric part of the crystal structures of 4, 5 one and two molecules are observed, respectively. In crystalline structures a flat nitro groups and carboxylic groups do not participate in the conjugation with aromatic rings. I structure of 4, an intermolecular C8-H...O9 hydrogen bond is observed, these H bonds link the molecules along the [010] axis. In the crystal structure of intermolecular C9B-H...O4A and C10B hydrogen bonds form chains along the [011 formed chains are cross linked by the intermolecular C9B-H...O5A hydrogen bonds.

t was carried out synthesis of esters and their dinitro trimethoxybenzoic (eudesmic) acid. Esterification of eudesmic acid carried out n absolute methanol or ethanol and corresponding trimethoxybenzoates (2, 3) ave been synthesized in good yields. It was revealed that nitration of these esters gives only dinitro products. The structure of the synthesized compounds methyl and ethyl 2,6-dinitro-3,4,5was determined by X-ray tion analysis (XRD). In the asymmetric part of one and two molecules are observed, respectively. In crystalline structures a flat nitro groups and carboxylic groups do not participate in the conjugation with aromatic rings. In (1). This natural carboxylic acid can be found in Eucalyptus spp. [1].
There is in medicine practice more than 20 drugs are successfully used, such as: antimuscarinic effect [2] and its maleic acid salt recutin, polybutin [3], trimetozine (sedative activity) [4,5] is used in Europe since 1959 and has been used in the treatment of anxiety [6,7], dilazep (vasodilator) acts as an adenosine reuptake inhibition [8], troxipide is a drug used in the treatment of gastroesophageal reflux disease and it is novel systematic non antisecretory gastric cytoprotective agent with anti ulser, anti-inflammatory properties [9 methoserpidine [15] is an related to reserpine and its analogues [16] some 3,4,5 trimethoxybenzoic acid derivatives have been synthesized and studied their activity on the central nervous system [17]. Discussion of literatures shows that 3,4,5-trimethoxybenzoic acid and its derivatives are very interest and important synthons for creation of pharmacologically active drugs.
Aim of this work is developing effective methods for synthesis of 2,6-dinitro-3,4,5 which has reactive carboxylic g There is in medicine practice more than 20 drugs are successfully used, such as: trimebutine with antimuscarinic effect [2] and its maleic acid saltrecutin, polybutin [3], trimetozine (sedative activity) [4,5] is used in Europe since 1959 and has been used in the treatment of anxiety [6,7], dilazep (vasodilator) reuptake inhibition [8], troxipide is a drug used in the treatment of gastroesophageal reflux disease and it is novel systematic nonantisecretory gastric cytoprotective agent with antiinflammatory properties [9][10][11][12][13][14], methoserpidine [15] is an antihypertensive drug related to reserpine and its analogues [16] some 3,4,5trimethoxybenzoic acid derivatives have been synthesized and studied their activity on the central nervous system [17]. Discussion of literatures shows c acid and its derivatives are very interest and important synthons for creation of pharmacologically active drugs.
Aim of this work is developing effective methods for 3,4,5-trimethoxybenzoic acid, which has reactive carboxylic group and studying their International Journal of Trend in Scientific Research and Development (IJTSRD) ISSN: 2456-6470 @ IJTSRD | Available Online @ www.ijtsrd.com | Volume -1 | Issue -6 | Sep-Oct 2017 Page: 177 x-ray structure. We can successfully use this synthones in the synthesis of many potential bioactive substances and for introduction of pharmacophoric fragments of eudesmic acid into molecules of different natural [18] and synthetic heterocyclic compounds [19]. These investigations will be presented in our next publications.

MATERIALS AND METHODS
1 Н NMR spectrum was recorded in acetone-d 6 on Varian 400-MR spectrometer operating accordingly at 400 MHz. Hexamethyldisiloxcane (HMDSO) was used as internal standard, chemical shift  of 1 H was recorded in ppm. Mps were measured on a Boetius and MEL-TEMP apparatus manufactured by Barnstead International (USA) and were uncorrected. IR spectra were recorded on IR Fury System 2000 (Perkin-Elmer) as KBr pellets.
The reactionary process was monitored by TLC on Whatman UV-254 precoated aluminum plates using CHCl 3 /CH 3 OH -10:1, C 6 H 6 /CH 3 OH -25:1 solvent system and developed plates were visualized under UV lamp and/or iodine tank where necessary. Solvents were purified by standard procedures. Organic solutions were dried over anhydrous Na 2 SO 4 and concentrated with a RVO-64 ROT VAC Evaporator at reduced pressure.
X-ray diffraction studies of compounds 4 and 5.
The crystals of compounds 4 and 5, suitable for X-ray diffraction, were grown by slow evaporation of solvent -EtOH at room temperature. The crystal cell parameters are determined and refined on a CCD Xcalibur Ruby (Oxford Diffraction) diffractometer using CuK-radiation. The correction for absorption was introduced by the Multi-scan method.
A CrysAlis Pro program package was used for the determination of cell parameters, data integration, scaling and absorption correction [21]. The structures were solved by direct methods (SHELXS-97) [22] and refined by full matrix least-square procedures on F 2 (SHELXL-97) [23]. The non-hydrogen atoms were refined anisotropically and hydrogen atoms were placed at idealized positions and refined using the riding model. A summary of the fundamental crystal and refinement data is provided in Table 2

CONCLUSIONS
It was carried out synthesis of dinitro derivatives of 3,4,5-trimethoxybenzoic (eudesmic) acid -methyl and ethyl 2,6-dinitro-3,4,5-trimethoxybenzoates (4, 5), which are important synthones in the organic and bioorganic chemistry. It was found that nitration of methyl and ethyl 3,4,5-trimethoxybenzoates (2, 3) by nitrating mixture corresponding dinitro productsmethyl and ethyl 2,6-dinitro-3,4,5trimethoxybenzoates (4, 5) are synthesized and their structures were determined by X-ray diffraction analysis (XRD). No formation of mono-nitro product was (6) observed. It was revealed that in the asymmetric part of the crystal structures of 4, 5 one and two molecules are observed. It was observed that in the crystalline structures a flat nitro groups and carboxylic groups do not participate in the conjugation with aromatic rings, and in the crystal structures of 4 and 5 an intermolecular hydrogen bond are observed, which these H bonds link the molecules along the [010] and [011] axis, respectively.