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Ring Expansion of 2-Alkylidenedihydroquinolines to 2-Iminodihydro-1-benzazepines by Phenyl, Methanesulphonyl, and Trifluoromethanesulphonyl Azide[1]

✍ Scribed by Helmut Quast; Svetlana Ivanova; Eva-Maria Peters; Karl Peters

Book ID: 102657901
Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 836 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200002)2000:3<507::aid-ejoc507>3.0.co;2-v

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✦ Synopsis

2-Alkyl-1-methylquinolinium hexafluorophosphates 1 are deprotonated by sodium or potassium hydride to afford solutions of 2-alkylidenedihydroquinolines 2, which are investigated by NMR spectroscopy. 1,3-Dipolar cycloaddition of phenyl azide to 2 yields the spirocyclic products 10. While, at 80Ϫ110 °C, the [3 + 2] cycloaddition that afforded (u)-10f is reversible and accompanied by epimerisation to give (l)-10f, thermolysis of the dimethyl compounds 10b and d affords the ring-expanded products 14b and d, respectively, in good yields along with molecular nitrogen. Irradiation of 10d with light of λ Ͼ 320 nm results in the formation of similar amounts of 14d and [3 + 2] cycloreversion products, viz. 2-

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