Визначення маскованої основності в імідазо[1,5-a]піридинкарбонових кислотах з використанням естерів
Imidazo[1,5-a]pyridine carboxylic acids are useful building blocks for medical chemistry, but their synthesis scale-up and isolation depend strongly on pH. For zwitterion-prone representatives, a direct titration of acids does not always reveal the basicity of the heteroaromatic center, which is cri...
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| Дата: | 2026 |
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| Автори: | , |
| Формат: | Стаття |
| Мова: | Англійська |
| Опубліковано: |
National University of Pharmacy
2026
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| Теми: | |
| Онлайн доступ: | https://ophcj.nuph.edu.ua/article/view/360150 |
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| Назва журналу: | Journal of Organic and Pharmaceutical Chemistry |
| Завантажити файл: |  |
Репозитарії
Journal of Organic and Pharmaceutical Chemistry| Резюме: | Imidazo[1,5-a]pyridine carboxylic acids are useful building blocks for medical chemistry, but their synthesis scale-up and isolation depend strongly on pH. For zwitterion-prone representatives, a direct titration of acids does not always reveal the basicity of the heteroaromatic center, which is critical for their further use. Therefore, a series of acids, their corresponding esters, and hydrochlorides were analyzed by the potentiometric titration together with 1H/13C NMR, HPLC, LCMS, and HRMS. The acids showed apparent pKa values of 5.13-6.11, while the esters exposed the basic-center pKa values in the range of 2.75-4.64. NMR data indicate close electronic similarity within the acid/ester pairs, supporting the use of esters as models for acids with masked basicity. |
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| DOI: | 10.24959/ophcj.26.360150 |