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

B Lee, P Kang, KH Lee, J Cho, W Nam, WK Lee…

Index: Lee, Byeongno; Kang, Philjun; Lee, Kyu Hyung; Cho, Jaeheung; Nam, Wonwoo; Lee, Won Koo; Hur, Nam Hwi Tetrahedron Letters, 2013 , vol. 54, # 11 p. 1384 - 1388

Full Text: HTML

Citation Number: 23

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 ...

~99%

~99%

~96%

~10%

Reductive amine deallyl-and debenzylation with alkali metal ...

[Nandi, Partha; Dye, James L.; Jackson, James E. Tetrahedron Letters, 2009 , vol. 50, # 27 p. 3864 - 3866]

Synthesis of β-tosylethylhydrazine and its use in preparatio...

[Dastrup, David M.; Yap, Amy H.; Weinreb, Steven M.; Henry, James R.; Lechleiter, Andrew J. Tetrahedron, 2004 , vol. 60, # 4 p. 901 - 906]

Straightforward transformation of isoxazoles into pyrazoles:...

[Sviridov, Sergey I.; Vasil'ev, Andrei A.; Shorshnev, Sergey V. Tetrahedron, 2007 , vol. 63, # 49 p. 12195 - 12201]

Radical scavenging by N-aminoazaaromatics

[Itoh, Takashi; Miyazaki, Michiko; Maeta, Hiromi; Matsuya, Yuji; Nagata, Kazuhiro; Ohsawa, Akio Bioorganic and Medicinal Chemistry, 2000 , vol. 8, # 8 p. 1983 - 1989]