New Approach to the Synthesis of 2‐Sulfonylaminosubstituted Imidazo[1,2‐<i>a</i>]pyridines via the Cascade Reaction of N‐(1‐aryl‐2,2,2‐trichloroethyl)sulfonamides with 2‐Aminopyridines

Serykh, V. Yu.; Ushakov, Igor А.; Bоrodinа, Tatyana N.; Смирнов, В. И.; Розенцвейг, И. Б.

doi:10.1002/slct.201902838

Cited by 3 publications

(1 citation statement)

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“…reported the synthesis of 3‐sulfonyl amino‐substituted imidazo[1,2‐ a ]pyridines [159] and other annelated imidazole derivatives from N ‐sulfonyl phenyl dichloro acetal dimines [160] . In continuation of this research, in 2019 they reported the synthesis of 2‐sulfonyl amino‐substituted imidazo[1,2‐ a ]pyridines 203 in the presence of K 2 CO 3 and DABCO from 2‐aminopyridine derivatives 202 and N ‐(1‐aryl‐2,2,2‐trichloroethyl)arene sulfonamides 201 in moderate to good yields [161] . The mechanism involves the formation of the chloroaziridine intermediate A .…”

Section: Development Of Various Methods Towards the Synthesis Of Imid...mentioning

confidence: 98%

Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

et al. 2022

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This review focuses on providing comprehensive highlights of the recent synthetic pathways of imidazo[1,2‐a]pyridines, assisted through transition metal‐catalyzed reactions, multi‐component reactions, cyclization, condensation, microwave‐assisted reactions, heteroannular and photocatalytic reactions. Among the heterocyclic groups, imidazo[1,2‐a]pyridines are considered as privileged structures because of their occurrence in many natural products. In this review, we have summarized the recent advances in the synthesis of imidazo[1,2‐a]pyridines from 2016 to 2021 from various substrates. This review will provide new initiatives to the chemists towards the synthesis of imidazo[1,2‐a]pyridines and all frequent challenges associated with the reported methods.

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Section: Development Of Various Methods Towards the Synthesis Of Imid...mentioning

confidence: 98%

Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

et al. 2022

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Five-membered ring systems: with more than one N atom

Yet

2021

Progress in Heterocyclic Chemistry

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Synthesis and properties of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide

Aizina,

Tkachuk,

Shaglaeva

2024

Izvestiâ vuzov. Prikladnaâ himiâ i biotehnologiâ

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The present work continues a systematic study to find efficient and accessible methods for the synthesis ofN-sulfonylimines of polyhaloaldehydes and to analyze their properties. In the reaction of N,N-dichlorobenzene sulfon-amide with tribromoethylene, N-(2,2,2-tribromoethylidene)amide of 4-chlorobenzenesulfonic acid was obtained for the first time with a quantitative yield at boiling water bath temperature in carbon tetrachloride medium. The infrared spectra of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide reveal the absorption bands of sulfonic (1360 and 1165 cm-1) and NH (3275 cm-1) groups, while the 1H NMR spectra show a signal for azomethine protons within the region of 8.3–8.6 ppm. The 13C NMR spectra exhibit a signal for the CBr3 group within the region of ~31–43 ppm, while the signal characteristic of the CBr2Сl group within the region of ~53–56 ppm is absent. This means that no imine of dibromochloroacetic aldehyde is formed during the reaction. Thus, an efficient method for the synthesis of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide was developed, and the chemoselectivity of this reaction was found to depend on the process temperature. It was shown that N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide has amidoalkylating properties. A reaction of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide with benzene, toluene, anisole, and 2-chlorothiophene in the presence of an acid catalyst yielded p-substituted aromatic derivatives and 2,5-substituted thiophene derivatives. Infrared spectroscopy and NMR spectroscopy (1H, 13C) revealed that the substitution reaction proceeds regioselectively. All the obtained products were isolated in pure form as powders soluble in polar organic solvents and insoluble in water. The yields of 4-chloro-N-(1-phenyl-2,2,2-tribromoethyl)-benzenesulfonamide, 4-chloro-N-[1-(4-methylphenyl)-2,2,2-tribromoethyl]-benzenesulfonamide, 4-chloro-N-[1-(4-methoxyphenyl)-2,2,2-tribromoethyl]-benzene-sulfonamide, and 4-chloro-N-[2,2,2-tribromoethyl-1-(5-chloro-2-thienyl)ethyl]-benzenesulfonamide amounted to 74, 72, 64, and 74 %, respectively.

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New Approach to the Synthesis of 2‐Sulfonylaminosubstituted Imidazo[1,2‐a]pyridines via the Cascade Reaction of N‐(1‐aryl‐2,2,2‐trichloroethyl)sulfonamides with 2‐Aminopyridines

Cited by 3 publications

References 62 publications

Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

Five-membered ring systems: with more than one N atom

Synthesis and properties of N-(2,2,2-tribromoethylidene)-4-chlorobenzenesulfonamide

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