Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole — National Research Tomsk Polytechnic University

Abstract

1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.

Original language	English
Pages (from-to)	843-846
Number of pages	4
Journal	Bulletin of the Academy of Sciences of the USSR Division of Chemical Science
Volume	18
Issue number	4
DOIs	https://doi.org/10.1007/BF00907056
Publication status	Published - 1 Apr 1969
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1007/BF00907056

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Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole. / Shvartsberg, M. S.; Vasilevskii, S. F.; Sagdeev, R. Z.; Kotlyarevskii, I. L.

In: Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 18, No. 4, 01.04.1969, p. 843-846.

Research output: Contribution to journal › Article › peer-review

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title = "Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole",

abstract = "1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.",

author = "Shvartsberg, {M. S.} and Vasilevskii, {S. F.} and Sagdeev, {R. Z.} and Kotlyarevskii, {I. L.}",

year = "1969",

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T1 - Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole

AU - Shvartsberg, M. S.

AU - Vasilevskii, S. F.

AU - Sagdeev, R. Z.

AU - Kotlyarevskii, I. L.

PY - 1969/4/1

Y1 - 1969/4/1

N2 - 1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.

AB - 1. A method was developed for the synthesis of 4-ethynyl-3,5-dimethylpyrazole from 4-acetyl-3,5-dimethylpyrazole. 2. The reaction of 4-acetyl-3,5-dimethylpyrazole with excess phosphorus pentachloride at elevated temperatures is anomalous and leads, in addition to replacement of the carbonyl oxygen by chlorine, to the replacement of hydrogen in the methyl group attached to the carbonyl group by chlorine. 3. On removal of hydrogen chloride with sodamide in liquid ammonia (3,5-dimethyl-4-pyrazolyl)-α,β-diehloroethylene gives a high yield of (3,5-dimethyl-4-pyrazolyl)-chloroacetylene.

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Acetylene derivatives of heterocycles - 5. Some peculiarities in the synthesis of 4-ethynyl-3,5-dimethylpyrazole

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