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Alpha vinylation of haloquinoline-5,8-diones with methyl acrylate and methyl vinyl ketone under baylis-hillman reaction conditions

✍ Scribed by Hyoung Seok Song; Young Seok Song; Kee-Jung Lee

Book ID
102338215
Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
339 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A synthesis of mono‐ and di‐vinylquinolinediones based on substitution of the halogens in 6,7‐dihaloquinoline‐5,8‐diones by DABCO‐assisted enolate ion is described. Divinylquinolines undergo 6π‐electrocyclization by thermally to give the benzo[g]quinoline derivatives.

📜 SIMILAR VOLUMES

α-Vinylation of Haloquinoline-5,8-diones
α-Vinylation of Haloquinoline-5,8-diones with Methyl Acrylate and Methyl Vinyl Ketone under Baylis—Hillman Reaction Conditions.
✍ Hyoung Seok Song; Young Seok Song; Kee-Jung Lee 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

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Baylis–Hillman reactions of N-arylidened
Baylis–Hillman reactions of N-arylidenediphenylphosphinamides with methyl vinyl ketone, methyl acrylate, and acrylonitrile
✍ Min Shi; Gui-Ling Zhao 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 70 KB

We have found that in the Baylis-Hillman reactions of N-arylidenediphenylphosphinamides 1 with methyl vinyl ketone (MVK), methyl acrylate or acrylonitrile, the Lewis base and solvent can significantly affect the reaction rate. Using PPh 3 as Lewis base in the reaction of 1 with MVK in DMF, THF or Me