261727-75-7Relevant academic research and scientific papers
Investigation on the formation of 6-hydroxyindole in the nenitzescu reaction. VI. Cyclization of β-[(1,4-quinon-2-yl)methyl]-enaminon derivatives
Kucklaender,Lessel
, p. 17 - 26 (2007/10/03)
Starting from 2,5-bisbenzyloxy-4-methyl-benzaldehyd 2-(3-amino-2-acetyl-but-2-enyl)-5-methyl[1,4]benzoquinones 9a-e are synthesized as model compounds in order to study the ambident reactivity of enaminones and quinones. Spontaneus cyclization of 9b-e in ethanol or acetic acid to 1-aza-spiro[4,5]deca-2,7-dien-6,9-dion 20b-e in good yield is observed. 6-Hydroxy-3-acetyl-quinoline 21 is obtained from 9a. In one case (9c) 2-acetyl-3-benzylamino-7-hydroxy-naphthalene (17) was formed as by-product. 9d in alkoholic perchloric acid leads to quinolinium salt 18 in low yield. Wiley-VCH Verlag GmbH, 2000.
