2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier–Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides

• Published in: Tetrahedron letters Vol. 56; no. 37; pp. 5164 - 5167
• Main Authors: Venkanna, P., Rajanna, K.C., Satish Kumar, M., Bismillah Ansari, Mohd, Moazzam Ali, M.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 09-09-2015
• Subjects: 2,4,6-Trichloro-1,3,5-triazine/N,N′-dimethylformamide; 2-Chloro-3-formyl quinolines; Acetanilides; Rate acceleration; Sonication; Vilsmeier–Haack type reagent; Vilsmeier–Haack type reagent; Sonication; 2,4,6-Trichloro-1,3,5-triazine/N,N′-dimethylformamide; Acetanilides; Rate acceleration; 2-Chloro-3-formyl quinolines
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.07.056

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TCTA–DMF (2,4,6-trichloro-1,3,5-triazine/N,N′-dimethylformamide) adduct has been used as a Vilsmeier–Haack type reagent for effective synthesis of 2-chloro-3-formyl quinolines from acetanilides under conventional and ultrasonically assisted conditions. The reaction times under sonication are quite significantly shorter than conventional methods even though the yields obtained under sonication are comparable with those obtained under reflux conditions.