Novel Synthesis of Functionalized Bis(Benzo‐Heterocyclic Amine) Derivatives via Copper‐Catalyzed One‐Pot Multicomponent Reactions
A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound...
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Veröffentlicht in: | ChemistrySelect (Weinheim) 2024-07, Vol.9 (27), p.n/a |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques.
The protocol detailed in the study for the copper‐catalyzed one‐pot synthesis of various substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine represents a significant advancement in synthetic methodology. By utilizing the intramolecular cyclization of iodophenol and 2‐aminobenzimidazoles (thiazoles/oxazoles) in the presence of trichloroacetonitrile adduct under ultrasound irradiation in MeCN have developed a novel approach to to access these important compounds efficiently. The method offers several advantages, including short reaction times, mild reaction conditions, straightforward work‐up procedures, and readily available starting materials and catalysts. |
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ISSN: | 2365-6549 2365-6549 |
DOI: | 10.1002/slct.202400871 |