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Ultrasound-assisted synthesis of highly functionalized benzo[1,3]thiazine via Cu-catalyzed intramolecular C–H activation reaction from isocyanides, aniline-benzoyl(acetyl) isothiocyanate adduct

Nematpour, M ; Sharif University of Technology | 2019

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  1. Type of Document: Article
  2. DOI: 10.1016/j.ultsonch.2018.08.001
  3. Publisher: Elsevier B.V , 2019
  4. Abstract:
  5. A facile sonochemical route for the synthesis of benzo[1,3]thiazine derivatives via a one pot, multicomponent, intramolecular C–H activation reaction from isocyanides, aniline and benzoyl (acetyl) isothiocyanate adduct catalyzed by copper (I) iodide in acetone at 30 °C have been reported. The advantages of the described method include using simple and readily available starting materials and performing under mild copper-catalytic reaction conditions and also obtaining pure product with high yield without applying column chromatography. Furthermore, using the sonochemical methodology as an efficient method led to reduce the reaction times. © 2018 Elsevier B.V
  6. Keywords:
  7. Aniline ; Benzo[1,3]thiazine ; Cu-catalyzed ; C–H activation ; Isocyanides ; Isothiocyanate ; Ultrasound-assisted ; Acetone ; Catalysis ; Chemical activation ; Column chromatography ; Cyanides ; Ultrasonics ; Catalytic reactions ; Copper iodide ; Functionalized ; Isothiocyanates ; Multicomponents ; Sonochemical ; Copper compounds ; 1,3 thiazine derivative ; 4 chloro n [6 chloro 4 (cyclohexylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; 4 chloro n [6 methyl 4 (phenylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; Benzo[1,3]thiazine derivative ; Copper ; Isothiocyanic acid derivative ; N [4 (cyclohexylimino) 6 methyl 1h benzo[d][1,3]thiazin 2(4h) ylidene]acetamide ; N [4 (phenylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; N [4 (tert butylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]acetamide ; N [4 (tert butylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; N [4 (tert butylimino) 6 nitro 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; N [6 bromo 4 (tert butylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]acetamide ; N [6 bromo 4 (tert butylimino) 1h benzo[d][1,3]thiazin 2(4h) ylidene]benzamide ; Unclassified drug ; Article ; Catalyst ; Chemical reaction ; Drug synthesis ; One pot synthesis ; Priority journal ; Reaction time ; Ultrasound ; Ultrasound assisted synthesis
  8. Source: Ultrasonics Sonochemistry ; Volume 50 , 2019 , Pages 1-5 ; 13504177 (ISSN)
  9. URL: https://www.sciencedirect.com/science/article/pii/S1350417718306758