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Heterocyclic spiro-naphthalenones. Part IV. Synthesis of some 3,4-dihydrospiro [naphthalene-2(1H),2′-pyrrolidine]-1-ols from 3,4-dihydrospiro [furan-2(5H),1′(2′H)-naphthalene]-2′,5-dione

✍ Scribed by Daniel Berney; Karlheinz Schuh

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
317 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Depending on the experimental conditions the spirolactone 3 on treatment with methylamine gave compounds 6, 7 or the rearranged product 4. Compound 4 was used to prepare the title compounds 11–13, 15, 18–20 and other derivatives.

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## Abstract The synthesis of specifically labeled 2,5,8‐trimethyl‐3,4‐dihydro‐1(2H)‐naphthalenone‐2‐d and 3,5,8‐trimethyl‐3,4‐dihydro‐1(2H)‐naphthalenone‐2,2‐d~2~ through α‐proton exchange using neat trifluoroacetic acid‐d is described.

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## Abstract The spirolactam **5** was reduced to the spiro[naphthalene, pyrrolidine] **7** which was __N__‐aralkylated to give **9** and **17**. Cyclization of **9** gave the phenanthridines **10** and **11**; similarly, **17** afforded the 7‐ and 8‐membered heterocycles **18** and **19**. Compound