Oxidation of enamine-esters with lead tetra-acetate. Part 1. Products from some N-alkylaminofumarates

Domino Reaction of 3-(2-Formylphenoxy)propenoates and Amines: A Novel Synthesis of 1,4-Dihydropyridines from Salicaldehydes, Ethyl Propiolate, and Amines

“…D then decomposes to enamine E and salicaldehyde ( 5 ). Finally, E cyclizes to 3 and releases amine, which is similar to Carr's synthesis of pyrroles .…”

Bulk Gold-Catalyzed Reactions of Diazoalkanes with Amines and O2 to Give Enamines

“…The 1 H NMR spectrum of (Z)-9 is the same as that reported in the literature [60] for this compound. The (E)-selectivity for the reaction of EDA with secondary amines is very similar to the reactions of dimethyl acetylenedicarboxylate (DMAD) with amines in which the (E)-configuration of the enamine esters was shown to be thermodynamically preferred [56][57][58][59]. The dominant (Z)-selectivity for primary amines is presumably due to the formation of a hydrogen bond between the free NH and the carbonyl oxygen as shown in Scheme 1, which was proposed by Iwanami as the reason for the formation of (Z)-enamines from the reactions of DMAD with primary amines [61].…”

“…10) (see Electronic Supplementary Material). The configurations of the (E)-and (Z)-isomers were established by comparison of their 1 H NMR spectral data with those of the dimethyl analogs reported by Vernon [58,59], Dolfini [62], and Saidi [63]. The (E)-enamines show a singlet near 4.7 ppm for the olefinic proton, while the (Z)-isomers show a singlet at about 5.1 ppm.…”

“…Enamine products were identified by comparison of their 1 H NMR spectra with those of authentic samples. These samples were prepared [56][57][58][59] as described in the Electronic Supplementary Material where 1 H and 13 C NMR and mass spectral data for all of the products are also given.…”