Regiospecific Three-Component Access to Fluorescent 2,4-Disubstituted Quinolines via One-Pot Coupling-Addition-Cyclocondensation-Sulfur Extrusion Sequence

2,4‐Di‐ and 2,4,7‐trisubstituted quinolines are readily synthesized in a regioselective fashion from acyl chlorides, terminal alkynes, and 2‐aminothiophenols by a consecutive, microwave‐assisted one‐pot three‐component Sonogashira coupling‐Michael addition–cyclocondensation sequence and following su...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2010-06, Vol.2010 (18), p.3516-3524
Main Authors: Rotzoll, Sven, Willy, Benjamin, Schönhaber, Jan, Rominger, Frank, Müller, Thomas J. J.
Format: Article
Language:English
Subjects:
C-C coupling
Chemistry
Computations
Exact sciences and technology
Fluorescence
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Microwave chemistry
Multicomponent reactions
Organic chemistry
Preparations and properties
Quinolines
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Summary:2,4‐Di‐ and 2,4,7‐trisubstituted quinolines are readily synthesized in a regioselective fashion from acyl chlorides, terminal alkynes, and 2‐aminothiophenols by a consecutive, microwave‐assisted one‐pot three‐component Sonogashira coupling‐Michael addition–cyclocondensation sequence and following sulfur extrusion in moderate to good yields. The terminal sulfur extrusion step was studied by DFT computations. The absorption spectra of 2,4‐disubstituted quinolines can be rationalized by DFT‐ZINDO‐CI calculations and all derivatives show intense blue emission upon UV excitation. 2,4‐Di‐ and 2,4,7‐trisubstituted quinolines are readily synthesized from acyl chlorides, terminal alkynes, and 2‐aminothiophenols by a consecutive, microwave‐assisted one‐pot three‐component coupling–cyclocondensation–sulfur extrusion sequence. The quinolines display intense blue fluorescence and their spectral properties can be rationalized by rapid DFT‐ZINDO‐CI calculations.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201000212