Nucleophilic Substitution of Hydrogen in Arenes and Heteroarenes

New pathways for the synthesis of indolyl-containing quinazoline trifluoroacetohydrazides

“…The structure of acylation products 7a,b was confirmed by 1 H, 13 Due to the fact, that the spectra of compounds 7a,b contain signals of the NHprotons of the indole fragment, it is obvious that the hydrazine part of the molecule undergoes acylation. 2D 1 H- 13 C HMBC spectra of compounds 7a,b contain characteristic intense cross-peaks between the carbon quartet of the trifluoroacetyl group (155.4 ppm, 2 J C-F = 36.7 Hz) and the N 1 H proton of the indole fragment (11.01 ppm). We believe that these cross peaks are due to the spin-spin interaction through the hydrogen bond (see Fig.…”

“…Since the signal of the NH-proton of the indole fragment is retained in adducts 6, it is obvious that the hydrazine part of the molecule undergoes acylation. It should be noted that the 2D 1 H- 13 C gHMBC spectra of adducts 6a,b contain intense cross peaks between the characteristic quartet of C8' atom in the trifluoroacetyl group, in particular, at 155.9 ppm for compound 6а ( 2 J С-F = 36.3 Hz), and the broadened signal of the N 1 H proton (see Fig. 1), indicating the presence of an intramolecular hydrogen bond N-H…O=C.…”

“…It should be noted that within the framework of this direction, atomic-economical reactions corresponding to the principles of green chemistry are a particular value [11]. This type of interactions includes nucleophilic reactions of C,Ccoupling under conditions of acid catalysis, which proceed without using of metal catalysts and are theoretically waste-free [12,13].…”

8-Hydroxy-5-nitroquinoline as a C-nucleophilic reagent in the reaction of C, C-coupling with quinazoline

“…Reactions of nucleophilic substitution of hydrogen in 5-nitroquinolines have been described, which proceed in the orthoposition to the nitro group in interaction with nucleophiles containing a vicarious group (vicarious substitution) [4]. The reaction of amination of nitroquinolines with trimethylhydrazinium iodide occured in a solution of anhydrous DMSO in the presence of potassium tert-butylate [5].…”

Ureas as new nucleophilic reagents for SNH amination and carbamoyl amination reactions in the 1,3,7-triazapyrene series

“…[1][2][3][4] The most common method for their preparation is nucleophilic aromatic substitution of halide or other nucleofugal groups under noncatalytic 5,6 or catalytic conditions. [7][8][9][10] In the case of electron-deficient substrates, such as azines and nitroarenes, the nucleophilic aromatic substitution of hydrogen (S N H ), 11,12 including its oxidative [13][14][15] and vicarious 16,17 versions, is an attractive alternative. An oxidative nucleophilic substitution of hydrogen enables one to carry out the process following the principles of green chemistry, such as atom efficiency, shorter synthesis, less hazardous chemicals, waste prevention, etc.…”