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

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 a...

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Bibliographic Details
Published inTetrahedron letters Vol. 54; no. 11; pp. 1384 - 1388
Main Authors Lee, Byeongno, Kang, Philjun, Lee, Kyu Hyung, Cho, Jaeheung, Nam, Wonwoo, Lee, Won Koo, Hur, Nam Hwi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.03.2013
Elsevier
Subjects
Azines
Chemistry
Chemistry, Organic
Physical Sciences
Pyrazoles
Pyridazinones
Science & Technology
Solid state reaction
Solvent-free conditions
Solvent-free conditions
Pyridazinones
Pyrazoles
Solid state reaction
Azines
ONE-POT SYNTHESIS
REACTIVITY
ALDEHYDES
CATALYST
EFFICIENT
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.12.106