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The experimental data on the sulfonylation of 4-amino-1Hpyrazoles with p-toluenesulfonyl chloride are given in the paper. New compounds were obtained: 3,5-dimethyl-4-tosylamino-1H-pyrazole, 3-methoxymethyl-5-phenyl-4-tosylamino-1H-pyrazole, 3-methoxymethyl-5-naphthyl-4-tosylamino-1H-pyrazole, 3-methyl-5-naphthyl-4-tosylamino-1H-pyrazole. The structure of sulfonylated aminopyrazoles was proved by IR, UV, 1H NMR spectroscopy and mass spectrometry.
Keywords: pyrazole, aminopyrazole, sulfonylamide, sulfonylation, NMR, IR, UV spectroscopy, mass spectrometry.
DOI: 10.17516/1998-2836-0026.
В статье приведены эκспериментальные данные по сульфонилированию 4-амино-1Н пиразолов п-толуолсульфохлоридом. Получены новые соединения: 3,5-диметил-4-тозиламино-1Н-пиразол, 3-метоκсиметил-5-фенил-4-тозиламино-1Н-пиразол, 3-метоκсиметил-5-нафтил-4-тозиламино-1Н-пиразол, 3-метил-5-нафтил-4-тозиламино-1Н-пиразол. Строение сульфонилированных аминопиразолов доκазано с помощью ИК, Уφ, ЯМР1Н спеκтросκопии и масс-спеκтрометрии.
Ключевые слова: пиразол, аминопиразол, сульфониламид, сульфонилирование, ЯМР1Н-, ИК-, Уφ-спеκтросκопия, масс-спеκтрометрия.
Introduction
An important priority for a person is to maintain healthy. Nowadays, there is a huge number of medicines in the world, but microbes progress with a great speed, constantly adapting to the activity of new drugs, and therefore the search and synthesis of new substances with antibacterial activity does not stop.
It is known that among the pyrazole derivatives there are a number of known highly effective drugs, such as antipyrine, analgin and others [1]. Therefore, new pyrazole derivatives by now continue to attract the attention of specialists engaged in the search for new effective biologically active substances, including chemical-pharmaceutical drugs, pesticides, bioprotectors for various materials, antioxidants, etc. Particularly interesting ones in this respect are amine-substituted pyrazoles. The disadvantages of known aminopyrazoles include their poor solubility and as a consequence the difficulty of removing the products of their metabolism from the body therefore they are toxic to the liver and kidneys, and also cause the manifestation of agranulocytosis [2].
Most often, amines are not used in a free form, but in the form of sulfonylated derivatives. So, sulfanilamide drugs are very widely used - a group of chemically synthesized compounds used for the treatment of infectious diseases, mainly of bacterial origin.
Sulfanilamides were the first drugs that allowed successful prevention and treatment of a variety of bacterial infections. Thanks to these drugs entered into medical practice since the 1930s, it was possible to significantly reduce the death rate from pneumonia, blood infection and many other bacterial infections. Their widespread use during the World War II saved many lives [3].
Therefore, the aim of our work was to obtain new sulfonyl derivatives of aminopyrazoles. Earlier at the department of organic chemistry and...