Synthesis of Substituted Coumarins and 2-Quinolinones via Cycloisomerization of Hydroxyl/Aminophenyl Propargyl Alcohols†
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Reddy, M S
Thirupathi, Nuligonda Babu, M H |
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| Date |
2013-03-07T10:32:27Z
2013-03-07T10:32:27Z 2012 |
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| Identifier |
European Journal of Organic Chemistry 2012, 2012(29), 5803–5809
http://hdl.handle.net/123456789/1024 |
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| Description |
A novel cycloisomerization strategy for coumarins and quinolinones is described. Addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins via 6-endo-dig-cycloisomerization of the intermediates 2-(hydroxyphenyl)-3-ethoxy-2-yn-1-ols. In the similar conditions2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted to latter with an acid treatment. N-protected intermediate 8 was isolated and was converted to quinolinone (In(OTf)3 or H2SO4) and 3-iodo-2-quinolinone (I2/H+).
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| Format |
452250 bytes
application/pdf |
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| Language |
en
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| Relation |
CDRI Communication No. 8285
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| Subject |
Cycloisomerization
Alkyne Coumarin Quinoline Quinolinone |
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| Title |
Synthesis of Substituted Coumarins and 2-Quinolinones via Cycloisomerization of Hydroxyl/Aminophenyl Propargyl Alcohols†
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| Type |
Article
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