Abstract |
Two novel routes based on [5C + 1N] annulations for the synthesis of 2,3-dihydrofuro[3,2-c] pyridines are described. Ammonium acetate (NH(4)OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl] cyclopropanes as a five- carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dimethylamino)alkenyl]-4,5-dihydrofurans as the five- carbon synthons, which involves a sequential intermolecular aza-addition, intramolecular aza-nucleophilic addition/elimination, and dehydration reaction.
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Authors | Peng Huang, Rui Zhang, Yongjiu Liang, Dewen Dong |
Journal | Organic letters
(Org Lett)
Vol. 14
Issue 20
Pg. 5196-9
(Oct 19 2012)
ISSN: 1523-7052 [Electronic] United States |
PMID | 23025242
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Pyridines
- Carbon
- Nitrogen
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Topics |
- Carbon
(chemistry)
- Hydrogenation
- Molecular Structure
- Nitrogen
(chemistry)
- Pyridines
(chemical synthesis)
- Stereoisomerism
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