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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
[Synthesis of muscopyridine and its analogs]
C Y Wang1, D Y Zhang, L Z Huang
1Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing.
Abstract:
Muscopyridine (1) is one of the odoriferous constituents of natural musk. 1 was prepared previously in very low yield in multisteps. We report here one-step preparation of muscopyridine and its analogs by the cross-coupling method. The cyclocoupling is effected by slow dropwise addition of a THF solution of di-Grignard reagent under nitrogen to a well stirred mixture of an equimolar quantity of a dichloropyridine in THF containing a catalytic amount of Ni (dppp)Cl2. The reaction mixture is stirred at 35-40 degrees C for up to 20 h. Analogs 2, 3 and 4 have also been prepared by this method. The structure of these products and intermediates are determined by UV, IR, MS, and 1HNMR spectral data.
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