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Perimidines: a unique $\pi$-amphoteric heteroaromatic system

Alexander Fedorovich Pozharskii 1
Alexander Fedorovich Pozharskii
, 
Anna Vasil'evna Gulevskaya 1
Anna Vasil'evna Gulevskaya
, 
Rosa M Claramunt 2
Rosa M Claramunt
, 
Ibon Alkorta 3
Ibon Alkorta
, 
José Elguero 3
José Elguero
1 Department of Organic Chemistry, Southern Federal University
2 Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Spain
3 Instituto de Química Médica, CSIC, Spain
10.1070/RCR4963
Published 30 November 2019
Review , RCR4963, Volume 89, Issue 11, 1204-1260
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Pozharskii A. F. et al. Perimidines: a unique $\pi$-amphoteric heteroaromatic system // Russian Chemical Reviews. 2019. Vol. 89. No. 11. pp. 1204-1260.
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Pozharskii A. F., Gulevskaya A. V., Claramunt R. M., Alkorta I., Elguero J. Perimidines: a unique $\pi$-amphoteric heteroaromatic system // Russian Chemical Reviews. 2019. Vol. 89. No. 11. pp. 1204-1260.
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TY - JOUR
DO - 10.1070/RCR4963
UR - https://rcr.colab.ws/publications/10.1070/RCR4963
TI - Perimidines: a unique $\pi$-amphoteric heteroaromatic system
T2 - Russian Chemical Reviews
AU - Pozharskii, Alexander Fedorovich
AU - Gulevskaya, Anna Vasil'evna
AU - Claramunt, Rosa M
AU - Alkorta, Ibon
AU - Elguero, José
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1204-1260
IS - 11
VL - 89
ER -
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@article{2019_Pozharskii,
author = {Alexander Fedorovich Pozharskii and Anna Vasil'evna Gulevskaya and Rosa M Claramunt and Ibon Alkorta and José Elguero},
title = {Perimidines: a unique $\pi$-amphoteric heteroaromatic system},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4963},
number = {11},
pages = {1204--1260},
doi = {10.1070/RCR4963}
}
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Pozharskii, Alexander Fedorovich, et al. “Perimidines: a unique $\pi$-amphoteric heteroaromatic system.” Russian Chemical Reviews, vol. 89, no. 11, Nov. 2019, pp. 1204-1260. https://rcr.colab.ws/publications/10.1070/RCR4963.
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Keywords

1,8-diaminonaphthalenes
aromaticity
basicity
dihydroperimidines
N-heterocyclic carbenes.
perimidin-2(3H)-ones
perimidin-2(3H)-thiones
perimidines
proton sponges
reactivity
synthesis
tautomerism
π-amphoteric properties

Abstract

Data on the physicochemical characteristics, theoretical calculations, reactivity and synthetic methods for perimidines are summarized. Although perimidine and some of its simple 2-substituted derivatives were obtained by Sachs back in 1909, their chemistry and key physical properties remained unknown until the early 1970s. Subsequent studies revealed many fundamental features of the perimidine system, previously not encountered in the heterocyclic series. The first comprehensive review on perimidines was published forty years ago. The period that has passed since 1980 led to the emergence of new directions and trends. Several hundred new publications have appeared, the generalization of which has become the main purpose of this article. This primarily concerns the obtaining of highly nucleophilic and stable perimidine carbenes, new methods of electrophilic substitution and oxidation, establishment of a close relationship between perimidines and proton sponges, and modern theoretical calculations. Based on perimidines, many different polycondensed systems have been obtained. Applied research has developed especially rapidly in recent years. Many new compounds based on perimidines related to chemosensors, analytical reagents, dyes, metal catalysts, electronic devices, nanotechnology, and medical chemistry have been proposed. Some information under review is presented as Supplementary Materials. It contains six tables, which include data on the basicity constants of perimidines, details of some synthetic methods for perimidines and fused analogs and also a list of biological activities of perimidines.

The bibliography includes 387 references.

Funders

Russian Foundation for Basic Research
20-03-00112
Ministerio de Ciencia e Innovación de España
PGC2018-094644-B-C2

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