Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5275901 | Tetrahedron Letters | 2007 | 5 Pages |
Abstract
A series of diazabicyclic derivatives were prepared in three to four steps from p-anisidine and p-nitrobenzaldehyde. The key step of the synthesis involved the acid-catalyzed coupling of 4-aminocoumarin or dimedone derivatives with amino alcohols 3 or 7 to give the ring-opened forms 4, 10, 12 and the ring-closed diazabicycles 5, 6, 9, 11. When 4-alkylaminocoumarins were used as the coupling reagents, the major cyclized product was N-dealkylated diazabicycle 5, rather than the corresponding N-alkylated products. Alternatively, compound 4 was cyclized by DDQ oxidation to produce quinone imine 13. The molecular structures of the synthesized compounds were characterized by X-ray crystallography.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jiun-Ting Lai, Pei-Yu Kuo, Yung-Her Gau, Ding-Yah Yang,