Synthesis, characterization, and crystal structure of 2-iodo-3,4,5-trimethoxybenzoic acid

Kolev, Iliyan; Petrova, Svetlana; Nikolova, Rositsa; Dimowa, L.; Shivachev, Boris

doi:10.1016/j.molstruc.2012.10.039

Cited by 5 publications

(3 citation statements)

References 34 publications

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“…The observed ν(C=O) frequency shift to higher wavenumbers in pI-3,4-DMBA (from 1672 to 1688 cm -1 ) is thought to be associated with the presence of an ortho-positioned iodine atom. Similar spectral behaviour was also observed in the case of ITMBA (7). At this stage, however, we cannot confirm the presence of a second iodine atom in the vacant meta position of the aromatic 3,4-DMBA nucleus.…”

Section: Resultssupporting

confidence: 54%

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Convenient method for one-pot synthesis of novel amidotrizoic acid radioisosteres

Hadzhieva,

Kolev

2022

Scripta Scientifica Pharmaceutica

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INTRODUCTION:The present study presents an effective one-pot protocol for the synthesis of triiodosubstituted aromatic (benzoic) acids -radiopaque analogues of amidotrizoic acid. For the production of the acids intended, I 2 /AgNO 3 couple was used as an effective iodinating reagent. Moreover, suitably substituted methoxybenzoic acid derivatives were selected as appropriate targets for iodination. The total iodine content in the final (crude) products was determined by Volhard's titrimetric method. Further details on the chemical structure of the reaction products were obtained by ATR-FTIR and 1 H NMR spectroscopy. AIM:The aim of the present study is to evaluate the effectiveness of a new method proposed for the synthesis of triiodo-substituted aromatic acids -analogues of the X-ray contrast amidotrizoic acid. MATERIALS AND METHODS:All necessary reagents and solvents for the study were purchased from Acros Organics, Fisher. The syntheses were performed under mild conditions using standard laboratory equipment. The infrared (IR) spectral instrument was a TENSOR II of Bruker (Germany), equipped with an ATR (Platinum) attachment. The total iodine content of the crude reaction products was assayed by a classical pharmacopoeial method. RESULTS: All aromatic acids were successfully iodinated with the reagent couple used. Unfortunately, it was found that the reaction products were mixtures of several compounds -partially and completely iodinated products. The presence of 2,6-diiodosubstituted acids in them was established by the appearance of a ν(C=O) band in the shortwave range (at over 1700 cm -1 ). The total iodine content in the final (crude) products was determined by Volhard's back titration method. CONCLUSION: The applied synthetic method allows the production of a mixture of partially and completely iodinated products, derivatives of the utilized aromatic acids -3,4-dimethoxybenzoic (3,4-DMBA) and 3,5-dimethoxybenzoic acid (3,5-DMBA). The presence of 2,6-diiodosubstituted acids in the products' composition was determined using ATR-FTIR spectroscopy. The reduced yield of the totally substituted products was associated with the lower activity of the iodinating reagent. However, the iodine content of one of the products thus obtained was found to be close to the expected triiodine one.

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Section: Resultssupporting

confidence: 54%

“…In the course of our previous researches, we were able to obtain two iodine-containing aromatic, derivatives of eudesmic, acids -2-iodo-3,4,5-trimethoxybenzoic (ITMBA) and 2,6-diiodo-3,4,5-trimethoxybenzoic acid (DITMBA) (7,8). In both cases, however, the most aggressive iodinating reagent possible -I 2 /AgOOCCF 3 couple -was used.…”

Section: Resultsmentioning

confidence: 99%

Convenient method for one-pot synthesis of novel amidotrizoic acid radioisosteres

Hadzhieva,

Kolev

2022

Scripta Scientifica Pharmaceutica

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“…Precision quartz resonators are additionally tuned during fabrication by grinding the plate surface and controlling the thickness of deposited electrodes. 2 Synthesis of the analyzed compound (2,6-diiodoeudesmic acid) was achieved by the synthetic procedure described in (9). The identity and purity of the obtained product was also successfully proven by 1 H and 13 C NMR and FTIR one of the Au electrodes of the quartz plate from a toluene solution using an automatic micropipette.…”

Section: Methodsmentioning

confidence: 99%

A quartz crystal microbalance-assisted method for the assessment of iodine content in organoiodines

Kolev

Koseva

Marinov³

et al. 2019

Scripta Scientifica Pharmaceutica

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INTRODUCTION: A new experimental quantitative approach for evaluating iodine content in organoiodine compounds has been proposed, based on the quartz crystal microbalance (QCM) method. This approach relies on following the time behavior of the resonance frequency of the quartz plate under temperature activation of iodine-containing analyte deposited on its surface. MATERIALS AND METHODS: We have applied the QCM method and the pharmacopoeial titrimetric method. RESULTS AND CONCLUSION: From the mass variations observed, the quantity of emitted iodine is precisely obtained, which readily delivers its initial content in the studied sample. The obtained value corresponds exactly to the theoretical prediction, in contrast to the value obtained by applying the conventional pharmacopoeial metrics.

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Spectral behavior peculiarities of the carboxyl functional group in iodine encirclement - the case of 2,6-diiodo-3,4,5-trimethoxybenzoic acid

Kolev

Hadzhieva

Rogozherov

2021

Journal of Molecular Structure

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Synthesis, characterization, and crystal structure of 2-iodo-3,4,5-trimethoxybenzoic acid

Cited by 5 publications

References 34 publications

Convenient method for one-pot synthesis of novel amidotrizoic acid radioisosteres

Convenient method for one-pot synthesis of novel amidotrizoic acid radioisosteres

A quartz crystal microbalance-assisted method for the assessment of iodine content in organoiodines

Spectral behavior peculiarities of the carboxyl functional group in iodine encirclement - the case of 2,6-diiodo-3,4,5-trimethoxybenzoic acid

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