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Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols

Svetlana Konstantinovna Polyakova 1, 2
Svetlana Konstantinovna Polyakova
, 
Tatyana Vilar'evna Balashova 1
Tatyana Vilar'evna Balashova
, 
Roman Valeryevich Rumyantcev 1
Roman Valeryevich Rumyantcev
, 
Maxim Vyacheslavovich Arsenyev 1, 2
Maxim Vyacheslavovich Arsenyev
, 
Georgy Konstantinovich Fukin 1
Georgy Konstantinovich Fukin
, 
Sergey Arturovich Chesnokov 1
Sergey Arturovich Chesnokov
10.1016/j.mencom.2021.03.040
Published 2021-03-03
Communication , Volume 31, Issue 2, 262-264
8
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Polyakova S. K. et al. Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 262-264.
GOST all authors (up to 50) Copy
Polyakova S. K., Balashova T. V., Rumyantcev R. V., Arsenyev M. V., Fukin G. K., Chesnokov S. A. Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 262-264.
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TY - JOUR
DO - 10.1016/j.mencom.2021.03.040
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.040
TI - Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols
T2 - Mendeleev Communications
AU - Polyakova, Svetlana Konstantinovna
AU - Balashova, Tatyana Vilar'evna
AU - Rumyantcev, Roman Valeryevich
AU - Arsenyev, Maxim Vyacheslavovich
AU - Fukin, Georgy Konstantinovich
AU - Chesnokov, Sergey Arturovich
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 262-264
IS - 2
VL - 31
ER -
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@article{2021_Polyakova,
author = {Svetlana Konstantinovna Polyakova and Tatyana Vilar'evna Balashova and Roman Valeryevich Rumyantcev and Maxim Vyacheslavovich Arsenyev and Georgy Konstantinovich Fukin and Sergey Arturovich Chesnokov},
title = {Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.040},
number = {2},
pages = {262--264},
doi = {10.1016/j.mencom.2021.03.040}
}
MLA
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Polyakova, Svetlana Konstantinovna, et al. “Utilizing o-quinone methide chemistry: synthesis of sterically hindered acridin-4-ols.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 262-264. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.040.

Keywords

acridines
alkylation
anilines
catechols
heterocyclization
quinone methides
X-ray diffraction analysis

Abstract

Three new sterically hindered acridin-4-ols have been prepared by alkylation of anilines with 3,5-di-tert-butyl-6-methoxymethylcatechol followed by oxidation of the reaction mixture. Formation of the acridine moiety was found to occur in the course of oxidation of the intermediate (anilinomethyl)catechol on contact with air in the Et2O/H2O–KOH system. The molecular structure of two acridin-4-ols was determined by single-crystal X-ray diffraction.

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