Highly efficient AgNO₃‐catalyzed approach to 2‐(benzo[d]azol‐2‐yl)phenols from salicylaldehydes with 2‐aminothiophenol, 2‐aminophenol and benzene‐1,2‐diamine

Abstract

A new, convenient and efficient AgNO 3 -catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63-98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO 3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.

Features of the Molecular Structure and Luminescence of Rare-Earth Metal Complexes with Perfluorinated (Benzothiazolyl)phenolate Ligands

“…The dihedral angles between benzothiazole and hydroxyphenyl fragments are 1.09–7.35°. This feature is in excellent agreement with previously published non-fluorinated analogues [26,27,28]. Such conformation, similar to non-fluorinated analogues [26,27,28,29], is stabilized by an intramolecular hydrogen bond O(1)H(1)···N(1) [1.71(2) Å] (Figure 2).…”

Direct Oxygenation of C–H Bonds through Photoredox and Palladium Catalysis

“…4o was obtained as a yellow solid (52 mg, 63%); mp 199–203 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.80 (d, J = 8.6 Hz, 1H), 8.08 (d, J = 8.2 Hz, 1H), 7.98 (d, J = 7.9 Hz, 1H), 7.86 (dd, J = 8.5, 4.8 Hz, 2H), 7.64 (dd, J = 8.7, 6.9 Hz, 1H), 7.56 (t, J = 7.7 Hz, 1H), 7.44 (q, J = 7.9 Hz, 2H), 7.34 (dd, J = 8.9, 1.5 Hz, 1H); 13 C­{ 1 H} NMR (151 MHz, CDCl 3 ) δ 166.6, 158.9, 149.6, 133.8, 132.8, 131.1, 129.5, 128.6, 128.1, 126.8, 125.3, 123.6, 122.5, 121.7, 121.1, 119.8. Spectral data matched with the literature report …”

“…Spectral data matched with the literature report. 57 2-(Benzo [d]oxazol-2-yl)phenol (4p). Compound 4p was prepared according to the general reaction condition (ix).…”

Reversible Switching Based on Truly Intramolecular Long-Range Proton Transfer─Turning the Theoretical Concept into Experimental Reality

“…HQBT , a new compound, never synthesized or studied before, was obtained by the reaction of 7-hydroxyquinoline-8-carbaldehyde with 2-aminothiophenol in the presence of a catalytic amount of silver nitrate in dimethyl sulfoxide (DMSO) at 60 °C. HNBT was synthesized by the reaction of 2-hydroxynaphthaldehyde with 2-aminothiophenol in the presence of a catalytic amount of silver nitrate in DMSO at 40 °C . Details about the synthetic procedure and the structural characterization of the obtained compounds are given in the Supporting Information.…”