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A new entry to the preparation of pyrrolo[2,3-b]quinolines by an aza Wittig/electrocyclic ring-closure/nitrene insertion process

✍ Scribed by Pedro Molina; Julián Alcántara; Carmen López-Leonardo


Book ID
104207617
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
350 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis


A new method for the preparation of the pyrrolo[2,3-b]quinoline ring system involving the sequential formation of the pyridine ring (electrocyclic ring-closure) and the pyrrole (nitrene insertion reaction) rings. This approach is based on the regioselective formation of the iminophosphorane 2 from the bis(azide) 1, followed by aza Wittig reaction with isocyanates and further thermal treatment.


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✍ Pedro Molina; Mateo Alajarín; Angel Vidal 📂 Article 📅 1991 🏛 Elsevier Science 🌐 French ⚖ 266 KB

Aza Wittlg-type reactIonof~bu(rm~nophosphoranel I wrth one mole of-zsocyanate leads to the zmmophosphoranes 5 whrcti by treatment with a secondmok of-uocyanate affordedpyndo[2,3,Cde/qutnazo~nes 6 Smularly, reaction with ketenes leads to the formanon of benzo[del[l,6]naphthyrrdmes9 Direct converszon