Unexpected Cleavage of the N—N Bond in the Reactions of 3‐Pyrazolidinone‐1‐azomethine Imines with HCN.

Abstract

Pyrazole derivatives R 0180Unexpected Cleavage of the N-N Bond in the Reactions of 3-Pyrazolidinone-1-azomethine Imines with HCN. -Treatment of the title compounds with HCN is assumed to cause cycloaddition with formation of pyrazolo-triazole products. However, substrates (I) undergo an unexpected reaction to give products (III) resulting from β-eliminative N-N bond cleavage. In the case of the mesityl derivative (IV), the proposed intermediate is stable and can be isolated. -(PEZDIRC, L.; GROSELJ, U.; MEDEN, A.; STANOVNIK, B.; SVETE*, J.; Tetrahedron Lett. 48 (2007) 30, 5205-5208; Fac. Chem. Chem. Technol., Univ. Ljubljana,

A Tunable Route for the Synthesis of Azomethine Imines and β-Aminocarbonyl Compounds from Alkenes

“…Overall, these derivatization procedures establish that hydrazone 2h provides access to several types of β-aminocarbonyl compounds from simple alkenes. Finally, exploratory studies building on the [3 + 2] reactivity of closely related azomethine imines suggest the reactivity described herein holds potential for multicomponent reactions (eq ). …”

Microwave-assisted synthesis and antibacterial activity of some pyrazol-1-ylquinoxalin- 2(1H)-one derivatives

“…Although numerous methods are available for construction of pyrazoles [26,27], only little attention has been given to the pyrazolysis of quinoxalinone derivatives [28]. For instance, 1,3-dipolar cycloadditions of azomethine imines, available by acid catalyzed treatment of 3-pyrazolidinone with acetone and butyraldehyde, respectively, were studied [29]. The photoluminescence and electroluminescence of some new 1H-pyrazolo-…”