1. JCCT
  2. Всі випуски
  3. Випуск 17, Номер 2, 2023
  4. (1н-тетразол-1-іл)арендіазонієві солі як зручні реагенти для арилування хінонів: синтез 1,3-бензоксатіол-2-онів та нафто[2,1-d][1,3]оксатіол-2-онів, що містять (1н тетразол 1 іл)феніловий фрагмент

(1н-тетразол-1-іл)арендіазонієві солі як зручні реагенти для арилування хінонів: синтез 1,3-бензоксатіол-2-онів та нафто[2,1-d][1,3]оксатіол-2-онів, що містять (1н тетразол 1 іл)феніловий фрагмент

JCCT.
2023;
Випуск 17, Номер 2
: cc. 304 - 314
https://doi.org/10.23939/chcht17.02.304
Автори:
  1. Nazariy Pokhodylo
  2. Roman Martyak
  3. Mykola Тupychak
  4. Khrystyna Pitkovych
  5. Vasyl Matiychuk
  6. Mykola Obushak
1
Ivan Franko National University of Lviv
2
Ivan Franko National University of Lviv
3
Ivan Franko National University of Lviv
4
Ivan Franko National University of Lviv
5
Ivan Franko National University of Lviv
6
Ivan Franko National University of Lviv

Розроблено зручний двостадійний метод синтезу нових 1,3-бензоксатіол-2-онів і нафто[2,1-d][1,3]оксатіол-2-онів, що містять (1Н-тетразол-1-іл)феніловий фрагмент. Як ключовий етап синтезу було вивчено арилування хінонів (1,4-бензохінонів, 1,4-нафтохінонів) солями (1H-тетразол-1-іл)арендіазонію та розроблено ефективні методики для отримання різноманітних заміщених ((1Н-тетразол-1-іл)феніл)бензо/нафто-1,4-хінонів з хорошими або високими ви-ходами. Продемонстровано альтернативний синтез ((1Н-тетразол-1-іл)феніл)нафто-1,4-хінонів за допомогою реакції Дільса-Альдера тетразолілфеніл-1,4-бензохінонів. Отримані бензо/нафто-1,4-хінони легко реагують з тіосечовиною за кімнатної температури в присутності сильних мінеральних кислот з утворенням проміжних ізотіуронієвих солей, які циклізуються під час нагрівання, утворюючи 1,3-оксатіол-2-они з високим виходом.

тетразол
хінон
оксатіолон
арилування Меервейна
циклізація
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