Oxidative Dehydrogenative [2 + 3]-Cyclization of Glycine Esters with Aziridines Leading to Imidazolidines

Abstract

Oxidative dehydrogenative [2 + 3]-cyclization of glycine derivatives with N-sulfonylaziridines is described. A series of complex imidazolidines were produced under mild and simple reaction conditions. A mechanism involving an unusual acid-promoted auto-oxidation is proposed.

Oxidative Dehydrogenative [3+3] Annulation of Benzylhydrazines with Aziridines Leading to Tetrahydrotriazines

“…Our investigation began with optimization of the reaction of benzyl 2‐benzylhydrazinecarboxylate 1a with 2‐phenyl‐1‐tosyl‐ aziridine 2a (Scheme a). Under the similar reaction conditions of the ref , a product B was isolated. After overall screening, we found that the optimized reaction conditions for the coupling of two substrates include 10 mol% of copper acetate as the dehydrogenation catalyst under aerobic conditions, 20 mol% of boron trifluoride diethyl etherate as the nucleophilic ring opening catalyst, and dichloromethane as solvent under room temperature.…”

“…Very recently, our group achieved an oxidative dehydrogenative [2+3]‐cyclization of secondary amines with N ‐sulfonylaziridines to deliver substituted imidazolidines . We questioned if the substrates secondary amines were replaced with secondary hydrazines, as shown in Scheme , the method has the potential to produce triazine derivatives through [3+3] manner or N ‐amino imidazolidine derivatives through [2+3] manner.…”

Synthesis of functional 2-substituted 1,3-dinitroimidazolidines. A new synthetic approach to high-energy compounds

“…However, there are few data on the synthesis of analogous structures. [25][26][27][28] Acid 1 was synthesized by three methods. In the first method (Method A), glyoxylic acid ethyl ester (2) was condensed with potassium ethylene-1,2-disulfamate (3) at pH=3.4 and 45-50°С to furnish potassium 2-(ethoxycarbonyl)imidazolidine-1,3-5 disulfonate (4), which was then nitrated with concentrated HNO3 at between -35°С…”

Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides

“…In 2018, Huo and co-workers utilized aziridines as novel nitrogen sources in oxidative cycloaddition processes with glycine derivatives. 70 Aziridines constitute masked 1,3-dipoles prone to undergo formal [3+2] cyclizations with dipolarophiles. Accordingly, they described the synthesis of imidazolidine compounds through a novel oxidative dehydrogenative reaction of N-arylglycine esters and Nsulfonylaziridines (Scheme 27).…”