Synthesis and Mechanistic Study of Steroidal Oxime Ethers |
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| Authors: | Kamlesh Sharma Shivani B Mishra Ajay K Mishra |
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| Institution: | 1. Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits, 2050, Johannesburg, South Africa (phone: +27‐720‐260988);2. Department of Chemical Technology, University of Johannesburg, Doornfontein 2028, Johannesburg, South Africa |
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| Abstract: | Reaction of 5α‐cholestan‐6‐one oxime ( 1 ), its 3β‐acetoxy and 3β‐chloro analogs, 2 and 3 , respectiveley, with ClCH2CH2NH2?HCl in presence of MeONa afforded 6‐(2‐aminoethoxy)imino]‐5α‐cholestane ( 4 ), 3β‐acetoxy‐6‐(2‐aminoethoxy)imino]‐5α‐cholestane ( 5 ), and 6‐(2‐aminoethoxy)imino]‐3β‐chloro‐5α‐cholestane ( 6 ), respectively. The structures of newly synthesized compounds have been established on the basis of physical, analytical, and spectral data. Theoretical calculations were assessed by using DFT at B3LYP/6‐31G* level to describe the mechanism of the reaction. The stability and feasibility of all the generated structures studied in this report were supported by their respective fundamental frequencies and energy minima. |
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| Keywords: | Steroids Density‐functional theory (DFT) Oxime ethers |
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