Reversal of polarity by catalytic SET oxidation: synthesis of azabicyclo[m.n.0]alkanes via chemoselective reduction of amidines

Abstract

A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this...

Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles

“…D THF, and toluene for reactions were distilled under an atmosphere ether (PE), used here, refers to the 60-90 °C boiling point fraction o etate is abbreviated as EA. 1 H NMR and 13 C NMR spectra were r Avance/600 ( 1 H: 600 MHz, 13 C: 151 MHz) or Bruker Avance/400 ( 1 MHz at 25 °C). Fluorine nuclear magnetic resonance ( 19 F NMR) spe a Bruker Avance/600 spectrometer or a Bruker Avance/400.…”

“…Fluorine nuclear magnetic resonance ( 19 F NMR) spe a Bruker Avance/600 spectrometer or a Bruker Avance/400. 1 H NM brated against residual CHCl3 in the solvent (7.26 ppm). 13 C NMR sp against the peak of the residual CHCl3 in the solvent (77.2 ppm).…”

“…13 C NMR sp against the peak of the residual CHCl3 in the solvent (77.2 ppm). sented as follows: chemical shift (ppm), multiplicity (s = singlet, d = = quartet, and m = multiplet), coupling constant in hertz (Hz), and resolution mass spectra (HRMS) were measured on a mass spectr trospray ionization orthogonal acceleration time-of-flight (ESI-OA of all samples used for HRMS (>95%) was confirmed by 1 H NMR a scopic analysis. All reactions were monitored by thin-layer chrom EA = 10:1) with GF254 silica gel-coated plates.…”

“…Ethyl acetate is abbreviated as EA. 1 H NMR and 13 C NMR spectra were recorded on a Bruker Avance/600 ( 1 H: 600 MHz, 13 C: 151 MHz) or Bruker Avance/400 ( 1 H: 400 MHz, 13 C: 101 MHz at 25 • C). Fluorine nuclear magnetic resonance ( 19 F NMR) spectra were recorded on a Bruker Avance/600 spectrometer or a Bruker Avance/400.…”

“…Saturated N-heterocycles such as 3-azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds with a broad spectrum of activity against various bacteria, mycobacteria, parasites, tumors, and neurological disorders (Figure 1) [1][2][3][4][5][6][7][8][9]. For example, Duocarmycin SA, Yatakemycin, and CC-1065 are representative members of such well-known biomolecules that derive their antitumor activity from their ability to alkylate DNA [10].…”