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Search Results (4)

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Keywords = SNAr rearrangement

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19 pages, 1247 KB  
Article
Reductive Cyclization of N-Alkyl- and N-Aryl-N-(2-Nitrophenyl) Amides to 1,2-Disubstituted Benzimidazoles
by Nash E. Nevels, Matthew E. Germond and Richard A. Bunce
Molecules 2026, 31(12), 2150; https://doi.org/10.3390/molecules31122150 - 18 Jun 2026
Viewed by 497
Abstract
A new three-step strategy for the preparation of 1,2-disubstituted 1H-benzo[d]imidazoles has been developed. The approach involved (1) SNAr addition-elimination of alkyl- or arylamines to 1-fluoro-2-nitrobenzene to give N-alkyl- or N-aryl-2-nitroanilines, (2) acylation of these adducts [...] Read more.
A new three-step strategy for the preparation of 1,2-disubstituted 1H-benzo[d]imidazoles has been developed. The approach involved (1) SNAr addition-elimination of alkyl- or arylamines to 1-fluoro-2-nitrobenzene to give N-alkyl- or N-aryl-2-nitroanilines, (2) acylation of these adducts with acid chlorides to afford N-alkyl- or N-aryl-N-(2-nitrophenyl) amides, and (3) reduction of the aromatic nitro with iron in acetic acid at 95–100 °C, followed by closure of the resulting amine on the amide carbonyl to produce 1,2-disubstituted benzimidazoles in high yields. The sequence gave the benzimidazole products in NMR-pure form with only one purification after Step 2. Thirty-seven derivatives were prepared, providing a broad selection of 1,2-disubstituted benzimidazoles. Interestingly, the reaction of the aniline nitrogen derived from the reduction of the nitro group afforded the final product by addition to the acyl carbonyl, followed by dehydrative aromatization with no competing rearrangement, acyl transfer, or side products. Full article
(This article belongs to the Special Issue Feature Papers in Organic Chemistry—Third Edition)
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10 pages, 3385 KB  
Communication
Hydroxide-Mediated SNAr Rearrangement for Synthesis of Novel Depside Derivatives Containing Diaryl Ether Skeleton as Antitumor Agents
by Xiang Yu, Yinkai Xi, Yi Sui, Yang Liu, Guifen Chen, Minjie Zhang, Yan Zhang, Guoyong Luo, Yi Long and Wude Yang
Molecules 2023, 28(11), 4303; https://doi.org/10.3390/molecules28114303 - 24 May 2023
Cited by 5 | Viewed by 2730
Abstract
A simple and efficient hydroxide-mediated SNAr rearrangement was reported to synthesize new depside derivatives containing the diaryl ether skeleton from the natural product barbatic acid. The prepared compounds were determined using 1H NMR, 13C NMR, HRMS, and X-ray crystallographic [...] Read more.
A simple and efficient hydroxide-mediated SNAr rearrangement was reported to synthesize new depside derivatives containing the diaryl ether skeleton from the natural product barbatic acid. The prepared compounds were determined using 1H NMR, 13C NMR, HRMS, and X-ray crystallographic analysis and were also screened in vitro for cytotoxicity against three cancer cell lines and one normal cell line. The evaluation results showed that compound 3b possessed the best antiproliferative activity against liver cancer HepG2 cell line and low toxicity, which made it worth further study. Full article
(This article belongs to the Special Issue Biological Activity of Natural and Synthetic Compounds 2.0)
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16 pages, 3204 KB  
Article
Straightforward and Efficient Protocol for the Synthesis of Pyrazolo [4,3-b]pyridines and Indazoles
by Vladislav V. Nikol’skiy, Mikhail E. Minyaev, Maxim A. Bastrakov and Alexey M. Starosotnikov
Int. J. Mol. Sci. 2023, 24(2), 1758; https://doi.org/10.3390/ijms24021758 - 16 Jan 2023
Cited by 5 | Viewed by 3542
Abstract
An efficient method for the synthesis of pyrazolo [4,3-b]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via a sequence of SNAr and modified Japp–Klingemann reactions. The method offers a number of advantages including utilization of stable arenediazonium tosylates, [...] Read more.
An efficient method for the synthesis of pyrazolo [4,3-b]pyridines has been developed on the basis of readily available 2-chloro-3-nitropyridines via a sequence of SNAr and modified Japp–Klingemann reactions. The method offers a number of advantages including utilization of stable arenediazonium tosylates, operational simplicity as well as combining the azo-coupling, deacylation and pyrazole ring annulation steps in a one-pot manner. An unusual rearrangement (C-N-migration of the acetyl group) was observed and a plausible mechanism was proposed based on the isolated intermediates and NMR experiments. In addition, the developed protocol was successfully applied to the synthesis of 1-arylindazoles combining the Japp–Klingemann reaction and cyclization of the resulting hydrazone as a one-pot procedure. Full article
(This article belongs to the Special Issue Polynitrogen and Nitrogen-Oxygen Molecular Systems: Synthesis, Reactivity and Application)
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29 pages, 725 KB  
Review
Recent Syntheses of 1,2,3,4-Tetrahydroquinolines, 2,3-Dihydro-4(1H)-quinolinones and 4(1H)-Quinolinones using Domino Reactions
by Baskar Nammalwar and Richard A. Bunce
Molecules 2014, 19(1), 204-232; https://doi.org/10.3390/molecules19010204 - 24 Dec 2013
Cited by 137 | Viewed by 16468
Abstract
A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures [...] Read more.
A review of the recent literature is given focusing on synthetic approaches to 1,2,3,4-tetrahydroquinolines, 2,3-dihydro-4(1H)-quinolinones and 4(1H)-quinolinones using domino reactions. These syntheses involve: (1) reduction or oxidation followed by cyclization; (2) SNAr-terminated sequences; (3) acid-catalyzed ring closures or rearrangements; (4) high temperature cyclizations and (5) metal-promoted processes as well as several less thoroughly studied reactions. Each domino method is presented with a brief discussion of mechanism, scope, yields, simplicity and potential utility. Full article
(This article belongs to the Special Issue Domino Reactions)
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