Tetrahedron

Studies on the synthesis of amidoximes from nitroalkanes

G Sanguineti, HV Le, B Ganem

Index: Sanguineti, Gabriella; Le, Hoang V.; Ganem, Bruce Tetrahedron, 2011 , vol. 67, # 52 p. 10208 - 10211

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Abstract

As part of our ongoing effort to expand the repertoire of synthetically useful multicomponent reactions (MCRs), we recently disclosed a new synthesis of substituted indoles from nitroalkanes and arylhydrazines in the presence of base. 1 The success of the method relied on transforming the derived nitronate anion 2 (Scheme 1) either to the monoprotonated aci-nitro species 3 or to the di-protonated iminium species 4, with subsequent hydrazine addition and N/N interchange to produce ...