Home / Publications / A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine

A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine

Larisa Vasil'evna Èktova 1
Larisa Vasil'evna Èktova
, 
Fedor Anatol'evich Zhuravlev 1
Fedor Anatol'evich Zhuravlev
10.1070/MC1993v003n01ABEH000205
Published 1993-02-28
Communication , Volume 3, Issue 1, 23-24
2
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Èktova L. V., Zhuravlev F. A. A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine // Mendeleev Communications. 1993. Vol. 3. No. 1. pp. 23-24.
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Èktova L. V., Zhuravlev F. A. A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine // Mendeleev Communications. 1993. Vol. 3. No. 1. pp. 23-24.
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TY - JOUR
DO - 10.1070/MC1993v003n01ABEH000205
UR - https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000205
TI - A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine
T2 - Mendeleev Communications
AU - Èktova, Larisa Vasil'evna
AU - Zhuravlev, Fedor Anatol'evich
PY - 1993
DA - 1993/02/28
PB - Mendeleev Communications
SP - 23-24
IS - 1
VL - 3
ER -
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@article{1993_Èktova,
author = {Larisa Vasil'evna Èktova and Fedor Anatol'evich Zhuravlev},
title = {A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine},
journal = {Mendeleev Communications},
year = {1993},
volume = {3},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000205},
number = {1},
pages = {23--24},
doi = {10.1070/MC1993v003n01ABEH000205}
}
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Èktova, Larisa Vasil'evna, and Fedor Anatol'evich Zhuravlev. “A Smiles Rearrangement as an Intermediate Step in the Formation of 8-Bromo-7-hydroxy-N-(4’ -N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-lmine from 2-(2’ -Aminophenylthio)-6-bromo-5-hydroxy-N-(4-/V,/V-diethylaminophenyl)-1,4-naphthoquinone 4-lmine.” Mendeleev Communications, vol. 3, no. 1, Feb. 1993, pp. 23-24. https://mendcomm.colab.ws/publications/10.1070/MC1993v003n01ABEH000205.

Abstract

Heating 2-(2’-aminophenylthio)-6-bromo-5-hydroxy-N(4’-N,N-diethylaminophenyl)-1,4-naphthoquinone 1 in DMF-Py leads, along with the product of cyclization at the carbonyl group, to formation of 8-bromo-7-hydroxy- /V-(4’-N,N-diethylaminophenyl)-12H-benzo[b]phenothiazine-6,11-quinone 6-imine 4 via a Smiles rearrangement in the starting quinone imine and subsequent cyclization.

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