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Heterocyclic Spiro-naphthalenones. Part III. Synthesis and reactions of some spiro [naphthalene-1,2′-pyrrolidin]-2-ones and spiro [naphthalene-2,2′-pyrrolidin]-1-ones

✍ Scribed by Daniel Berney; Karlheinz Schuh


Publisher
John Wiley and Sons
Year
1979
Tongue
German
Weight
450 KB
Volume
62
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

The spironaphthalen‐2‐ones 2, 10 and 18 were prepared by N‐bromosuccinimide (NBS) oxidation of 1, 9 and 17 respectively, whereas spironaphthalen‐1‐ones 24 and 25 were obtained by treating 23 with NBS.

The stereoisomeric reduction products 29, 30 and 32 obtained from 24 and 25, gave the pentacyclic compound 33 on treatment with polyphosphoric acid.


📜 SIMILAR VOLUMES


Heterocyclic Spiro-naphthalenones. Part
✍ Daniel Berney; Karlheinz Schuh 📂 Article 📅 1978 🏛 John Wiley and Sons 🌐 German ⚖ 334 KB 👁 1 views

## Abstract The spiro‐lactone **3** was obtained by __N__‐bromosuccinimide (NBS) oxidation of the carboxylate **2** at − 20°. When **2** was oxidized at 10° the spiro‐lactone **4** was the main product. Compound **4** was rearranged with triethylamine to the spiro‐lactone **9** whereas the stereois

Heterocyclic Spiro-naphthalenones. Part
✍ Daniel Berney; Karlheinz Schuh 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 379 KB

## 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

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✍ Daniel Berney; Karlheinz Schuh 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 317 KB

## 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.

Heterocyclic Spiro-naphthalenones. Part
✍ Daniel Berney; Karlheinz Schuh 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 179 KB 👁 1 views

## Abstract Compound **2** was rearranged on treatment with 2N NaOH to the 2‐benzazepine‐3‐propanoicSee footnote (5) of the preceding paper. acid **3**. Some aspects of the chemistry of this acid were studied.