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Optimised procedures for the one-pot selective syntheses of indoxyls and 4-quinolones by a carbonylative Sonogashira/cyclisation sequence

Paper ID Volume ID Publish Year Pages File Format Full-Text
42279 45918 2009 8 PDF Available
Title
Optimised procedures for the one-pot selective syntheses of indoxyls and 4-quinolones by a carbonylative Sonogashira/cyclisation sequence
Abstract

A selective one-pot synthesis of carbonyl-containing N-heterocyclic compounds has been developed using a carbonylative Sonogashira/cyclisation sequence. Various catalytic protocols were studied (CO pressure, temperature, catalyst identity, base and substrate/catalyst ratio) with the objective of obtaining selectively either indoxyl or 4-quinolone products. The origin of the selectivity toward the 5- or 6-membered ring compounds was explained through the respective role of the various catalytic species involved, whether they are organic or metallic. The non-cyclic common intermediate was selectively prepared using [PdCl2(dppp)] as catalyst. By using a two-step multi-catalysis, i.e. {[Pd]+HNEt2}, 4-quinolones were obtained whereas with a tandem catalysis, i.e. {[Pd]/PR3}, indoxyls were synthesised.

Graphical abstractA selective one-pot synthesis of carbonyl-containing N-heterocycles has been developed using a carbonylative Sonogashira/cyclisation sequence. The origin of the selectivity toward the 5- or 6-membered ring compounds was explained through the respective role of the palladium and amine or phosphine catalytic species involved.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
4-Quinolones; Indoxyls; One-pot synthesis; Carbonylative Sonogashira; Palladium catalysis
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Optimised procedures for the one-pot selective syntheses of indoxyls and 4-quinolones by a carbonylative Sonogashira/cyclisation sequence
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 369, Issues 1–2, 15 November 2009, Pages 125–132
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us