Abstract
A simple and efficient method was developed for the synthesis of 2,6-dihydropyrano[2,3-c]pyrazoles I [R = H, F, Br] via ring-closing metathesis (RCM) of 4-ethenyl-1-aryl-3-[(prop-2-en-1-yl)oxy]-1H-pyrazoles II using Grubbs' first generation catalyst. The required diene substrates II for the RCM reaction were prepd. by a three-step procedure starting from 1-aryl-1H-pyrazol-3-ols. The structures of the obtained heterocyclic products were unequivocally confirmed by detailed 1H, 13C, 15N and 19F NMR spectroscopic expts. and HRMS measurements. The optical properties of compd. I [R = H] were studied by UV-Vis and fluorescence spectroscopy.
Original language | English |
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Pages (from-to) | 3679-3690 |
Number of pages | 12 |
Journal | Tetrahedron |
Volume | 74 |
Issue number | 27 |
DOIs | |
Publication status | Published - 5 Jul 2018 |
Austrian Fields of Science 2012
- 104015 Organic chemistry
Keywords
- One-pot synthesis
- Pyridine
- Quinoline
- Indole
- Indolizine
- Imidazo[1,2-a]indole
- Pyrrolo[1,2-a]indole
- MULTICOMPONENT SYNTHESES
- AROMATIC-ALDEHYDES
- CRYSTAL-STRUCTURES
- DERIVATIVES
- 1-(2-PYRIDYL)-2-PROPEN-1-OL
- REARRANGEMENT
- INDOLIZINES
- CYCLIZATION
- CHEMISTRY
- CHLORIDE