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Regioselective synthesis of pentacyclic polyheterocycles: Sequential [3,3] sigmatropic rearrangement of 4-(4′-aryloxybut-2′-ynyloxy)-1-phenyl-1,8-naphthyridin-2(1H)-ones

✍ Scribed by Krishna C. Majumdar; Rafique-ul-Islam

Book ID
102339264
Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
353 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A number of 4‐aryloxymethyl‐6‐phenyl‐2__H__‐pyrano[3,2‐c][1,8]naphthyridin‐5(6__H__)‐ones (4a‐f) are regioselectively synthesized in 72‐78% yield by the Claisen rearrangement of 4‐(4′‐aryloxybut‐2′‐ynyloxy)‐1‐phenyl‐1,8‐naphthyridin‐2(1__H__)‐ones (3a‐f) in refluxing chlorobenzene for 4‐6 h. These products are then subjected to a second Claisen rearrangement catalyzed by anhydrous AlCl~3~ at room temperature for 2 h to give hitherto unreported pentacyclic heterocycles (5a‐f) in 78‐85% yield.

📜 SIMILAR VOLUMES

Regioselective Synthesis of Pentacyclic
Regioselective Synthesis of Pentacyclic Polyheterocycles: Sequential [3,3] Sigmatropic Rearrangement of 4-(4′-Aryloxybut-2′-ynyloxy)-1-phenyl-1,8-naphthyridin-2(1H)-ones.
✍ Krishna C. Majumdar; Rafique-ul-Islam Rafique-ul-Islam 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 24 KB 👁 1 views

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