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

Authors

  • Игорь Л. Никонов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108
  • Павел А. Слепухин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108
  • Дмитрий С. Копчук Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108
  • Игорь С. Ковалев Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Григорий В. Зырянов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108
  • Анна И. Суворова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Олег С. Ельцов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002
  • Владимир Л. Русинов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108
  • Олег Н. Чупахин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

DOI:

https://doi.org/10.1007/5116

Keywords:

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

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

Author Biographies

Игорь Л. Никонов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

Младший научный сотрудник, Уральский Федеральный Университет

Павел А. Слепухин, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

cтарший научный сотрудник, Институт Органического Синтеза

Дмитрий С. Копчук, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

научный сотрудник, Группа координационных соединений

Игорь С. Ковалев, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Младший научный сотрудник, Уральский Федеральный Университет

Григорий В. Зырянов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

cтарший научный сотрудник, Группа координационных соединений

Олег С. Ельцов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002

Доцент, Уральский Федеральный Университет

Владимир Л. Русинов, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

Зав кафедро ОиБХ,

Уральский Федеральный Университет

Олег Н. Чупахин, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002 Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi /20 Akademicheskaya St., Yekaterinburg 620108

Научный руководитель

Институт Органического Синтеза

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Published

2019-11-12

Issue

Vol. 55 No. 11 (2019)

Section

Short Communications