| Budget Amount *help |
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2013: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
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| Research Abstract |
The reductive rearrangement of various cyclic and acyclic oximes with aluminum reductants (DIBALH, AlHCl2 etc.) was performed to afford various secondary amines. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an aromatic ring.
The reaction proceeds through a three-centered transition state via a stepwise mechanism, because the potential energy curve along the intrinsic reaction coordinate had two maxima and the partial phenonium cation intermediate. The preference of the migration of a substituent was clarified that the more electron-rich group migrated preferentially to give the corresponding compounds. Their application to synthetic studies of several candidate compounds (AVP antagonist, 17 beta-HSD inhibitor, URAT-1 inhibitor) for clinical studies was demonstrated. Therefore, this reaction could be of practical use for the synthesis of fine chemistry and medicinal chemistry.
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