期刊
TETRAHEDRON LETTERS
卷 50, 期 1, 页码 51-54出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.10.083
关键词
2-Naphthol; Naphthopyrans; 3H-Benzo[f]chromenes; 2,2-Dialkyl-3-dialkylamino-1,2-dihydro-1H-naphtho[2,1-b]pyrans; Quinone methide; Microwave-assisted synthesis; Cyclization
资金
- Natural Sciences and Engineering Research Council of Canada
- Acadia University
2,2-Dialkyl-3-dialkylamino-2,3-dihydro-1H-naphtho[2,1-b]pyrans were prepared from 2-naphthol, a secondary amine, and 3-hydroxy-2,2-dialkylpropanal in the presence of a catalytic amount of p-toluenesulfonic acid. This one-pot reaction involves retro-aldol disintegration of 3-hydroxy-2,2-dialkylpropanal followed by formation of a Mannich base intermediate from 2-naphthol, a secondary amine, and formaldehyde (retro-aldol product). This Mannich base then disproportionates into a quinone methide intermediate and the secondary amine is regenerated. It then forms an enamine intermediate with 2,2-dialkylacetalclehyde (another retro-aldol product). Finally, the quinone methide intermediate undergoes electrocyclic ring closure with enamines to produce the title compounds. (C) 2008 Elsevier Ltd. All rights reserved.
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