A Novel and Efficient Synthesis of 3‐[(4,5‐Dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐chromen‐2‐ones (=3‐[(4,5‐Dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐1‐benzopyran‐2‐ones)
An efficient one‐pot synthesis of 3‐[(4,5‐dihydro‐1 H ‐pyrrol‐3‐yl)carbonyl]‐2 H ‐chromen‐2‐one (=3‐[(4,5‐dihydro‐1 H ‐pyrrol‐3yl)carbonyl]‐2 H ‐1‐benzopyran‐2‐one) derivatives 4 by a four‐component reaction of a salicylaldehyde 1 , 4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one, a benzylamine 2 , and a diaroy...
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Veröffentlicht in: | Helvetica chimica acta 2013-03, Vol.96 (3), p.473-477 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | An efficient one‐pot synthesis of 3‐[(4,5‐dihydro‐1
H
‐pyrrol‐3‐yl)carbonyl]‐2
H
‐chromen‐2‐one (=3‐[(4,5‐dihydro‐1
H
‐pyrrol‐3yl)carbonyl]‐2
H
‐1‐benzopyran‐2‐one) derivatives
4
by a four‐component reaction of a salicylaldehyde
1
, 4‐hydroxy‐6‐methyl‐2
H
‐pyran‐2‐one, a benzylamine
2
, and a diaroylacetylene (=1,4‐diarylbut‐2‐yne‐1,4‐dione)
3
in EtOH is reported. This new protocol has the advantages of high yields (
Table
), and convenient operation. The structures of these coumarin (=2
H
‐1‐benzopyran‐2‐one) derivatives, which are important compounds in organic chemistry, were confirmed spectroscopically (IR,
1
H‐ and
13
C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (
Scheme 2
). |
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ISSN: | 0018-019X 1522-2675 |
DOI: | 10.1002/hlca.201200216 |