Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine

Byeongno Lee; Philjun Kang; Kyu Hyung Lee; Jaeheung Cho; Wonwoo Nam; Won Koo Lee; Nam Hwi Hur

doi:10.1016/j.tetlet.2012.12.106

Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine

Byeongno Lee, Philjun Kang, Kyu Hyung Lee, Jaeheung Cho, Wonwoo Nam, Won Koo Lee, Nam Hwi Hur

Department of Chemistry & Nanoscience

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

52 Scopus citations

Abstract

Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97%) by grinding solid hydrazine (H₃N ⁺NHCO₂^-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright

Original language	English
Pages (from-to)	1384-1388
Number of pages	5
Journal	Tetrahedron Letters
Volume	54
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2012.12.106
State	Published - 13 Mar 2013

Bibliographical note

Funding Information:
N.H.H. thanks the Korea CCS R&D centre grant (20120008890) and the Converging Research Centre Program (2012K001486) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea . W.K.L. acknowledges the financial support ( NRF-2010-0005538 and NRF-2009-0081956 ) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea. B.L. thanks the Research Fellow Program (2012R1A12043256) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea.

Keywords

Azines
Pyrazoles
Pyridazinones
Solid state reaction
Solvent-free conditions

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10.1016/j.tetlet.2012.12.106

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title = "Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine",

abstract = "Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97\%) by grinding solid hydrazine (H3N +NHCO2-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright",

keywords = "Azines, Pyrazoles, Pyridazinones, Solid state reaction, Solvent-free conditions",

author = "Byeongno Lee and Philjun Kang and Lee, \{Kyu Hyung\} and Jaeheung Cho and Wonwoo Nam and Lee, \{Won Koo\} and Hur, \{Nam Hwi\}",

note = "Funding Information: N.H.H. thanks the Korea CCS R\&D centre grant (20120008890) and the Converging Research Centre Program (2012K001486) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea . W.K.L. acknowledges the financial support ( NRF-2010-0005538 and NRF-2009-0081956 ) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea. B.L. thanks the Research Fellow Program (2012R1A12043256) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea. ",

year = "2013",

month = mar,

day = "13",

doi = "10.1016/j.tetlet.2012.12.106",

language = "English",

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pages = "1384--1388",

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T1 - Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine

AU - Lee, Byeongno

AU - Kang, Philjun

AU - Lee, Kyu Hyung

AU - Cho, Jaeheung

AU - Nam, Wonwoo

AU - Lee, Won Koo

AU - Hur, Nam Hwi

N1 - Funding Information: N.H.H. thanks the Korea CCS R&D centre grant (20120008890) and the Converging Research Centre Program (2012K001486) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea . W.K.L. acknowledges the financial support ( NRF-2010-0005538 and NRF-2009-0081956 ) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea. B.L. thanks the Research Fellow Program (2012R1A12043256) funded by the Ministry of Education, Science, and Technology through the National Research Foundation of Korea.

PY - 2013/3/13

Y1 - 2013/3/13

N2 - Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97%) by grinding solid hydrazine (H3N +NHCO2-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright

AB - Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97%) by grinding solid hydrazine (H3N +NHCO2-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright

KW - Azines

KW - Pyrazoles

KW - Pyridazinones

KW - Solid state reaction

KW - Solvent-free conditions

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DO - 10.1016/j.tetlet.2012.12.106

M3 - Article

AN - SCOPUS:84874937196

SN - 0040-4039

VL - 54

SP - 1384

EP - 1388

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine

Abstract

Bibliographical note

Keywords

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