Weak base-promoted selective rearrangement of oxaziridines to amides via visible-light photoredox catalysis

Abstract

The selective rearrangement of oxaziridines to amides via single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amides via...

Convenient Synthesis of Benziodazolone: New Reagents for Direct Esterification of Alcohols and Amidation of Amines

“…N -(tert- butyl)-3-chlorobenzamide 10d [ 46 ]. The reaction of tert -butyl amine 9d (11 mg, 0.150 mmol) according to the general procedure afforded 14 mg (43%) of product 10d , isolated a white solid; 1 H NMR (400 MHz, CDCl 3 ): δ 7.69 (t, J = 2.0 Hz, 1H), 7.61–7.56 (m, 1H), 7.46–7.42 (m, 1H), 7.35 (t, J = 7.8 Hz, 1H), 5.92 (brs, 1H), and 1.47 (s, 9H); 13 C NMR (100 MHz, CDCl 3 ): δ 165.5, 137.8, 134.6, 131.1, 129.8, 127.1, 124.9, 51.9, and 28.8; HRMS (ESI-positive): calcd for C 11 H 14 ClNO ([M + H]) + : 212.0837, found: 212.0853.…”

Chemistry of Gold(III) with a Pyridine‐Oxaziridine Ligand: Competition between C−O and N−O bond Activation

“…[1][2][3][4][5] In some cases the oxaziridines may act as donors of the NR group or they may take part in cycloaddition reactions. [1,2] The strain in the 3-membered ring causes the oxaziridines to have limited stability and they may undergo thermal or photochemical decomposition, either by cleavage of the OÀ N bond to give (after proton transfer) the amide B or by cleavage of the OÀ C bond to give the nitrone C. [6][7][8][9] Under hydrolytic conditions, these primary decomposition products can react further to give acids D or aldehydes E (Scheme 1).…”

Facile preparation of N-tert-butyl amides under heat-, metal- and acid-free conditions by using tert-butyl nitrite (TBN) as a practical carbon source

“…The product 2a was characterized using NMR and mass analysis (ESI †). 20 The effect of solvent was then investigated (Table 1, entries 2-7). Of the examined organic solvents, CH 2 Cl 2 produced 2a with the best yield, of 57%, albeit with a rather long reaction time (Table 1, entries 2-7).…”

“…S1, ESI †). 20 Afterwards, a wide variety of nitriles (1) were investigated under the optimized reaction conditions to study the substrate scope of this methodology for the synthesis of N-tert-butyl amides (2), and the outcomes are summarized in Table 2. The reactions using various aliphatic nitriles indeed afforded the expected N-tert-butyl amides (2b-2h) in good yields (Table 2).…”