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PREPARATION OF 1-DICHLOROMETHYL- AND 1-TRICHLOROMETHYLISOQUINOLINES BY A ONE-STEP REACTION OF 1,2,4-TRIAZINES WITH 1,2-DEHYDROBENZENE

Игорь Л. Никонов, Павел А. Слепухин, Дмитрий С. Копчук, Игорь С. Ковалев, Григорий В. Зырянов, Анна И. Суворова, Олег С. Ельцов, Владимир Л. Русинов, Олег Н. Чупахин
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Abstract


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.

Authors: Igor L. Nikonov, Pavel A. Slepukhin, Dmitry S. Kopchuk, Igor S. Kovalev, Grigory V. Zyryanov*, Anna I. Suvorova, Oleg S. Eltsov, Vladimir L. Rusinov, Oleg N. Chupakhin


Keywords


aryne intermediates; 1-dichloromethylisoquinolines; 1,2,4-triazines; 1-trichloromethylisoquinolines; aza-Diels–Alder reaction; X-ray structural analysis

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