Journal
GREEN CHEMISTRY
Volume 17, Issue 1, Pages 460-465Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4gc01615g
Keywords
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Funding
- Thailand Research Fund [TRF-RSA5780055]
- National Nanotechnology Center (NANOTEC)
- NSTDA
- Ministry of Science and Technology, Thailand
- Thai Government Stimulus Package 2 [TKK2555, SP2]
- Higher Education Research Promotion and National Research University Project of Thailand, Office of the Higher Education Commission [AM1006A-56]
- Ratchadaphiseksomphot Endowment Fund of Chulalongkorn University [RES560530126-AM]
- Chulalongkorn University fund
- Ratchadaphiseksomphot Endowment Fund
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In this work, a novel synthetic methodology for the preparation of aryl pyrroles directly from the reaction of calcium carbide with oxime is reported. Various pyrrole derivatives are generated from the corresponding oximes in satisfactory yields (49-88%) under the optimized conditions. The one- pot synthesis of aryl pyrrole from widely available ketone is also successfully developed. A new near-infrared fluorescent BODIPY dye containing a phenyl substitution at the C-3 position is expediently prepared from the aryl pyrrole derived from this methodology. The key benefit of this methodology is the use of an inexpensive and less hazardous primary chemical feedstock, calcium carbide, in a wet solvent without any metal catalysts. This process offers a novel cost-efficient route for the synthesis of functionalized pyrrole.
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