Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: synthesis of methoxytropolones and furans.
Yvonne D Williams, Christine Meck, Noushad Mohd, Ryan P Murelli
Index: J. Org. Chem. 78(23) , 11707-13, (2013)
Full Text: HTML
Abstract
Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R(2) = R(3) = CO2Me) instead form furans as the major product.
Related Compounds
Related Articles:
2000-08-01
[J. Org. Chem. 65(15) , 4655-61, (2000)]
Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino) benzonitrile in alkane solvents. Demeter A, et al.
[Chem. Phys. Lett. 323(3) , 351-60, (2000)]
N-alkylation of hindered secondary aromatic amines with 2-iodobutane. Katritzky AR, et al.
[ORL J. Otorhinolaryngol. Relat. Spec. 23(4) , 399-402, (1991)]
Synthesis of N,N,N',N'-tetraalkylbenzidines through oxidative coupling of N,N-dialkylarylamines induced by SbCl5. Vitale P, et al.
[ARKIVOC 3 , 36-48, (2013)]