Regiospecific synthesis of 1-acetamide-5-methoxy-2-oxindoles in two steps: (Ugi-SN2)/xanthate mediated free radical cyclization |
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| Authors: | Angel Rentería-Gómez Alejandro Islas-JácomeJ Oscar C Jiménez-Halla Rocío Gámez-Montaño |
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| Institution: | Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato C.P. 36050, Gto., Mexico |
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| Abstract: | A series of twelve novel 1-acetamide-5-methoxy-2-oxindoles were prepared in moderate to good yields (30–88%) by an Ugi-SN2 one pot process with a xanthate mediated free radical cyclization. Additionally, Density Functional Theory (DFT) based calculations were performed at UB3LYP/6-311G(d) level in order to rationalize the energy profile of the xanthate mediated free radical cyclization because the benzo-fused γ-lactams (ortho products) were obtained as sole regioisomers over the spiro β-lactams (ipso products). |
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| Keywords: | 2-Oxindoles Multicomponent reactions Free radical cyclizations DFT calculations |
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