121868-75-5Relevant academic research and scientific papers
Investigations on the Formation of 6-Hydroxyindole in the Nenitzescu Reaction, II. - Cyclization of N-(Quinonylalkyl)enaminone Derivatives
Kucklaender, Uwe,Ulmer, Petra,Zerta, Gabriele
, p. 1493 - 1498 (2007/10/02)
The N-(quinonylethyl)enaminones 8a-d are synthesized from the phenylethylamines 5a,b.Quinones 8a,c,d are cyclized to the spiro compounds 9a,c,d.N-(Quinonylmethyl)enaminones 19a,b are obtained from aldehyde 12 via 13, 14, 15, and 16.Enaminone 19a cyclizes spontaneously to spiro compound 20.Ring closure of 19b yields isoquinolinium salts 21a,b.N-(Quinonylpropyl)enaminone 25 is gained from 22 via 23 and 24 and is O-protonated to 26.As shown by model reactions, primary 1,4-addition of enaminone nitrogen to p-benzoquinone is unlikely. - Keywords: Spirocyclization / Quinone cyclization / Enaminones / Nenitzescu reaction
