The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its deuterated analogue

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The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its deuterated analogue. / Ледовская, Мария Сергеевна ; Воронин, Владимир Владимирович.

в: Russian Journal of General Chemistry, Том 94, 17.12.2024, стр. 2833–2840.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{7fb4ee584fa2420fb32eb903ac5d862b,

title = "The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its deuterated analogue",

abstract = "The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its dideuterated analogue was performed using a novel two-step sequence. On the first step, a double chlorination of 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-hydrazineyl-1,2,4,5-tetrazine with trichlorocyanuric acid was performed to synthesize 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine for the first time. The latter reacted with calcium carbide-derived acetylene and D2-acetylene at heating in a two-chamber reactor (COware) producing 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine or 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-4,5-dideuteropyridazine respectively in quantitative yields.",

keywords = "1,2,4,5-tetrazine, pyridazine, chlorination, acetylene, Diels-Alder cycloaddition",

author = "Ледовская, {Мария Сергеевна} and Воронин, {Владимир Владимирович}",

year = "2024",

month = dec,

day = "17",

doi = "10.1134/S1070363224110033",

language = "English",

volume = "94",

pages = "2833–2840",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

}

RIS

TY - JOUR

T1 - The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its deuterated analogue

AU - Ледовская, Мария Сергеевна

AU - Воронин, Владимир Владимирович

PY - 2024/12/17

Y1 - 2024/12/17

N2 - The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its dideuterated analogue was performed using a novel two-step sequence. On the first step, a double chlorination of 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-hydrazineyl-1,2,4,5-tetrazine with trichlorocyanuric acid was performed to synthesize 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine for the first time. The latter reacted with calcium carbide-derived acetylene and D2-acetylene at heating in a two-chamber reactor (COware) producing 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine or 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-4,5-dideuteropyridazine respectively in quantitative yields.

AB - The synthesis of 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine and its dideuterated analogue was performed using a novel two-step sequence. On the first step, a double chlorination of 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-hydrazineyl-1,2,4,5-tetrazine with trichlorocyanuric acid was performed to synthesize 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine for the first time. The latter reacted with calcium carbide-derived acetylene and D2-acetylene at heating in a two-chamber reactor (COware) producing 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)pyridazine or 3-chloro-6-(4-chloro-3,5-dimethyl-1H-pyrazol-1-yl)-4,5-dideuteropyridazine respectively in quantitative yields.

KW - 1,2,4,5-tetrazine

KW - pyridazine

KW - chlorination

KW - acetylene

KW - Diels-Alder cycloaddition

UR - https://link.springer.com/article/10.1134/S1070363224110033

U2 - 10.1134/S1070363224110033

DO - 10.1134/S1070363224110033

M3 - Article

VL - 94

SP - 2833

EP - 2840

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

ER -

ID: 126740875