An original and convenient procedure has been proposed for one-step preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines in up to 40% yields via aza-Diels–Alder reaction of the readily available 3-dichloromethyl- and 3-trichloromethyl-1,2,4-triazines (in the role of dienes) with 1,2-dehydrobenzene (in the role of in situ generated dienophile). The structure of 1-trichloromethyl-4-phenylisoquinoline was confirmed by X-ray structural analysis.
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This work received financial support from the Russian Science Foundation (grant 18-13-00365).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1124–1127
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Nikonov, I.L., Slepukhin, P.A., Kopchuk, D.S. et al. Preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines by a one-step reaction of 1,2,4-triazines with 1,2-dehydrobenzene. Chem Heterocycl Comp 55, 1124–1127 (2019). https://doi.org/10.1007/s10593-019-02588-1
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DOI: https://doi.org/10.1007/s10593-019-02588-1