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Synthesis of Novel 3-Acyloxy-1,3-dihydro-2H-indol-2-ones and Isomeric 4-Acyl-1,4-dihydro-3,1-benzoxazin-2-ones: Double Rearrangement of 3-Hydroxyquinoline-2,4(1H,3H)-diones

✍ Scribed by Antonı́n Klásek; Kamil Kořistek; Jiřı́ Polis; Janez Košmrlj

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
172 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

Substituted 3-hydroxyquinoline-2,4(1H,3H )-diones 3 were transformed into 3-acyloxy-1,3-dihydro-2H-indol-2-ones 4 and isomeric 4-acyl-1,4-dihydro-3,1-benzoxazin-2-ones 5. The influence of the substituents and the reaction conditions on the course of the reaction was studied. In the proposed mechanism a double rearrangement takes place; a-ketol rearrangement of 3, leading to a-hydroxy-bdiketone intermediate 8, is followed by a rearrangement to the isomeric a-ketol-esters 4 and 5.

📜 SIMILAR VOLUMES

Ring Opening of 2-(Benzylamino)-2H-1,4-b
Ring Opening of 2-(Benzylamino)-2H-1,4-benzoxazin-3(4H)-ones and 2-Bromo-2H-1,4-benzoxazin-3(4H)-ones
✍ Janez Ilaš; Danijel Kikelj 📂 Article 📅 2008 🏛 John Wiley and Sons 🌐 German ⚖ 223 KB 👁 1 views

## Abstract Substituted 2‐(benzylamino)‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones are unstable under alkaline and acidic conditions, undergoing opening of the benzoxazinone ring. 2‐Bromo‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐ones show similar degradation under alkaline conditions, while replacement of Br at C