Arylhydrazines were treated with nitric oxide in tetrahydrofuran in the presence of oxygen to afford dehydrazinated compounds in good yields accompanied by small amounts of arylazides. 0 1997 Elsevier Science Ltd.
Nitric oxide (NO) is a gaseous radical molecule which has been revealed to play a variety of roles in biological functions.1 Because of the well-recognized importance of NO, extensive research has been carried out from the viewpoints of biochemistry and physiology.
In the area of chemistry, the reactivity of NO has attracted attention only in recent years, and papers concerning the chemistry of NO have been gradually increasing. The published reports seem to be classified into three types: employment of NO as a mild nitrosation or nitration reagent to exploit new organic reactions,2 development of the detection method of NO in a biological system using organic reactions,3 and reactions of NO with biologically important molecules. 4 In the course of our study of reactions using NO as a nitrosation reagent, it was revealed that Hantzsch dihydropyridines were readily aromatized by the use of NO as an oxidizing agent.5 Moreover, aromatic primary amines were found to react with NO in the presence of a catalytic amount of 02 in THF solution to bring about deamination reaction.6 These results suggested to us that compounds which contain an N-H bond might react with NO in various ways under the influence of 02.