67618-27-3Relevant academic research and scientific papers
Direct Amination of 9-Hydroxy-1-oxophenalene to Produce 9-Amino-1-oxophenalene and Related Compounds
Haddon, R. C.,Chichester, S. V.,Mayo, S. L.
, p. 639 - 641 (1985)
In connection with our studies of organo-non-metallic complexes of the 1,9-disubstituted phenalene unit 1 we required access to compounds possessing a total of just two ionizable hydrogen atoms in the A,B groups of 1.The prototypical compound in this series, 9-amino-1-oxophenalene (2), is not known although 9-hydroxy-1-oxophenalene (3) was first prepared in 1941 and a number of derivatives of 1 possessing one or three ionizable hydrogen atoms in the A,B groups have recently become available.We have found that the high-pressure reaction between 9-hydroxy-1-oxophenalene (3) and aqueous ammonia affords the desired 9-amino-1-oxophenalene (2) in high yield and good purity under relatively mild conditions.In addition 2 may be alkylated to produce the 9-amino-1-ethoxyphenalenylium salt which serves as a precursor for the other derivatives in this series with two ionizable hydrogen atoms in the A,B groups of 1.
1,9-Disubstituted phenalenes-I. Synthesis of n- and s-derivatives of 9-hydroxy-1-phenalenone
Franz,Martin
, p. 2147 - 2151 (2007/10/06)
The reaction of 9-hydroxy-1-phenalenone with Ag2O and alkyliodides gives the analogous β-keto-ethers from which synthetic pathways have been devised to isolate and characterise some nitrogen and sulphur derivatives. As intermediates stable phenalenium cations can be isolated by the reaction of 9-substituted 1-phenalenones with [(C2H5)3O]+BF4-. Whenever possible, a strong intramolecular H-bond is formed between the 1-and 9-substituents as shown by the low-field resonances of the respective hydrogens in the 1H NMR and the stability of the compounds towards reduction.
