One-Pot Synthesis of Highly Substituted 1H-Pyrazole-5-carboxylates from 4-Aryl-2,4-diketoesters and Arylhydrazines

Jiao Jiao Zhai; Chun Hui Gu; Ying Guo; Dao Hua Liao; Dun Ru Zhu; Ya Fei Ji

doi:10.1002/jhet.2354

One-Pot Synthesis of Highly Substituted 1H-Pyrazole-5-carboxylates from 4-Aryl-2,4-diketoesters and Arylhydrazines

Jiao Jiao Zhai, Chun Hui Gu, Ying Guo, Dao Hua Liao, Dun Ru Zhu, Ya Fei Ji

College of Chemical Engineering

East China University of Science and Technology

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

6 Scopus citations

Abstract

A one-pot synthesis of highly substituted 1H-pyrazole-5-carboxylates 1 has been developed starting from easily available 4-aryl-2,4-diketoesters 2 and arylhydrazine hydrochlorides 3. More active 2-carbonyl group of 2 was blocked with methoxyamine hydrochloride to give 2-methoxy imine intermediates, which were then subjected to condensation cyclization with 3 in situ to provide the desired products 1. In addition, the geometrical configuration of 1aa was unambiguously confirmed by single crystal X-ray crystallography.

Original language	English
Pages (from-to)	840-848
Number of pages	9
Journal	Journal of Heterocyclic Chemistry
Volume	53
Issue number	3
DOIs	https://doi.org/10.1002/jhet.2354
State	Published - 1 May 2016

Keywords

1H-Pyrazole-5-carboxylates
4-Aryl-2,4-diketoesters
Arylhydrazines
One-pot synthesis

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10.1002/jhet.2354

Cite this

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title = "One-Pot Synthesis of Highly Substituted 1H-Pyrazole-5-carboxylates from 4-Aryl-2,4-diketoesters and Arylhydrazines",

abstract = "A one-pot synthesis of highly substituted 1H-pyrazole-5-carboxylates 1 has been developed starting from easily available 4-aryl-2,4-diketoesters 2 and arylhydrazine hydrochlorides 3. More active 2-carbonyl group of 2 was blocked with methoxyamine hydrochloride to give 2-methoxy imine intermediates, which were then subjected to condensation cyclization with 3 in situ to provide the desired products 1. In addition, the geometrical configuration of 1aa was unambiguously confirmed by single crystal X-ray crystallography.",

keywords = "1H-Pyrazole-5-carboxylates, 4-Aryl-2,4-diketoesters, Arylhydrazines, One-pot synthesis",

author = "Zhai, {Jiao Jiao} and Gu, {Chun Hui} and Ying Guo and Liao, {Dao Hua} and Zhu, {Dun Ru} and Ji, {Ya Fei}",

note = "Publisher Copyright: {\textcopyright} 2015 HeteroCorporation.",

year = "2016",

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doi = "10.1002/jhet.2354",

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T1 - One-Pot Synthesis of Highly Substituted 1H-Pyrazole-5-carboxylates from 4-Aryl-2,4-diketoesters and Arylhydrazines

AU - Zhai, Jiao Jiao

AU - Gu, Chun Hui

AU - Guo, Ying

AU - Liao, Dao Hua

AU - Zhu, Dun Ru

AU - Ji, Ya Fei

PY - 2016/5/1

Y1 - 2016/5/1

N2 - A one-pot synthesis of highly substituted 1H-pyrazole-5-carboxylates 1 has been developed starting from easily available 4-aryl-2,4-diketoesters 2 and arylhydrazine hydrochlorides 3. More active 2-carbonyl group of 2 was blocked with methoxyamine hydrochloride to give 2-methoxy imine intermediates, which were then subjected to condensation cyclization with 3 in situ to provide the desired products 1. In addition, the geometrical configuration of 1aa was unambiguously confirmed by single crystal X-ray crystallography.

AB - A one-pot synthesis of highly substituted 1H-pyrazole-5-carboxylates 1 has been developed starting from easily available 4-aryl-2,4-diketoesters 2 and arylhydrazine hydrochlorides 3. More active 2-carbonyl group of 2 was blocked with methoxyamine hydrochloride to give 2-methoxy imine intermediates, which were then subjected to condensation cyclization with 3 in situ to provide the desired products 1. In addition, the geometrical configuration of 1aa was unambiguously confirmed by single crystal X-ray crystallography.

KW - 1H-Pyrazole-5-carboxylates

KW - 4-Aryl-2,4-diketoesters

KW - Arylhydrazines

KW - One-pot synthesis

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DO - 10.1002/jhet.2354

M3 - 文章

AN - SCOPUS:84931028054

SN - 0022-152X

VL - 53

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JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 3

ER -

One-Pot Synthesis of Highly Substituted 1H-Pyrazole-5-carboxylates from 4-Aryl-2,4-diketoesters and Arylhydrazines

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Keywords

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