ChemInform Abstract: The ((Methyloxy)imino)methyl Moiety as a Bioisoster of Aryl. A Novel Class of Completely Aliphatic β‐Adrenergic Receptor Antagonists.

Abstract

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Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides

“…Here, we focused on epoxidation of -unsaturated oximes. [11][12][13][14][15][16][17][18][19] We show herein that -unsaturated O-alkyl or O-silyl oximes readily react with electrophilic dioxiranes [20][21][22][23] to give -epoxy oximes in high yields. The results of ring opening of the epoxides with nucleophiles and an examination of Shi asymmetric epoxidation of the oximes are also reported (eq.…”

“…Since nucleophilic ring opening of epoxides is synthetically important, we next examined ring opening of epoxy oximes 4a-c. All epoxides reacted at the -position of the oxime functionalities, although -unsubstituted epoxy oximes have been reported to react at the -position (Table 2). 17,18) Thus, mild heating of epoxide 4a with sodium azide in DMF afforded -hydroxy -azide oxime 6a with trans-stereochemistry in 40% yield (entry 1). Oxime 4a also reacted with benzylamine in DMSO at 110 °C to give 7a in 84% yield (entry 2).…”

Bioisoterism Review- An Biological Modification

“…[39] The inversion of the atomic sequence of C=NOCH 2 of the MAOMM results in a different bioisostere, the [(methyloxy) imino] methyl moiety (CH 2 ON=C, MOIMM) [40] This moiety, in the E-configuration, has greater steric and electronic analogies to an aryl group as compared to MAOMM.…”