I have tried to use a bromine source to do an intramolecular cyclization with an amide to afford an Spiroisoxazolines containing lactam. But, the issue is that I believe it is not cyclizing because the lone pair from the nitrogen atom is doing resonance or abstract a proton from somewhere. I am trying to make a gamma-methylene gamma lactam by using three different synthetic methodology: Hg(OTf)2, amide and 1,2-diketone or make a anhydride and reduce one of the carbonyl groups to a methylene through a Wittig reaction. Please help!!!
Hi Cord,
can you maybe attach a scheme of what you try to do, it's somewhat difficult to get.
Regards,
Andrei
Hi Cord Carter
The following paper may be useful for you.
Bioorg Med Chem. 2010 Aug 1;18(15):5647-60. doi: 10.1016/j.bmc.2010.06.020. Epub 2010 Jun 15.
Synthesis, binding and bioactivity of gamma-methylene gamma-lactam ecdysone receptor ligands: advantages of QSAR models for flexible receptors.
Birru W1, Fernley RT, Graham LD, Grusovin J, Hill RJ, Hofmann A, Howell L, James PJ, Jarvis KE, Johnson WM, Jones DA, Leitner C, Liepa AJ, Lovrecz GO, Lu L, Nearn RH, O'Driscoll BJ, Phan T, Pollard M, Turner KA, Winkler DA.
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