6-Chloronicotinic acid was coupled by an amide linkage to Merrifield resin or Jeffamine gel. Nucleophilic displacement of the 6-chloride group by hydroxide gave novel Merrifield resin catalyst 6 or Jeffamine gel catalyst 9 that were successfully used for Henry condensations. The condensation of 4,6-O-benzylidene-β-D-glucopyranose 11 with nitromethane gave 4,6-O-benzylidene-D-glucopyranosyl-l-nitromethane 12; the condensation of 11 with nitroethane gave α-R-(4,6-O-benzylidene-β-D-glucopyranosyl)-1-nitroethane 13 and its diastereomer 15; the condensation of 11 with nitropropane, followed by acetylation, gave α-R-(2,3-di-O-acetyl-4,6-O-benzylidene-β- D-glucopyranosyl)-1 -nitropropane 16 and its diastereomer 17; the condensation of 4,6- O-isopropylidene-β-D-glucopyranose 19 with nitromethane gave 4,6-O-isopropylidene- β-D-glucopyranosyl-1-nitromethane 20; the condensation of 4,6-O-isopropylidene-α- D-mannopyranose 21 with nitromethane gave 4,6-O-isopropylidene-β-D-mannopyranosyl- 1-nitromethane 23. These known compounds were obtained with improved yields compared to protocols with 1,3 proton transfer catalysts that were not bound to polymers. A new monomeric 1,3 proton transfer catalyst, 2,4 (1,3)-quinazolinedione 10, was also introduced.
| Identifer | oai:union.ndltd.org:pacific.edu/oai:scholarlycommons.pacific.edu:uop_etds-3343 |
| Date | 01 January 1998 |
| Creators | Wan, Min |
| Publisher | Scholarly Commons |
| Source Sets | University of the Pacific |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | University of the Pacific Theses and Dissertations |
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