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Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives

Svetlana Gennad'evna Kachalkina 1
Svetlana Gennad'evna Kachalkina
, 
Gennadii Sergeevich Borodkin 2
Gennadii Sergeevich Borodkin
, 
Alexander Fedorovich Pozharskii 1
Alexander Fedorovich Pozharskii
, 
Alexander Sergeevich Antonov 1
Alexander Sergeevich Antonov
, 
Inna Gennadievna Borodkina 2
Inna Gennadievna Borodkina
, 
Yuri Fedorovich Maltsev 2
Yuri Fedorovich Maltsev
, 
Ekaterina Aleksandrovna Filatova 1
Ekaterina Aleksandrovna Filatova
, 
Aleksander Filarowski 3
Aleksander Filarowski
, 
Valery Anatol'evich Ozeryanskii 1
Valery Anatol'evich Ozeryanskii
10.1016/j.mencom.2015.05.007
Published 2015-04-28
Communication , Volume 25, Issue 3, 182-184
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Kachalkina S. G. et al. Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 182-184.
GOST all authors (up to 50) Copy
Kachalkina S. G., Borodkin G. S., Pozharskii A. F., Antonov A. S., Borodkina I. G., Maltsev Y. F., Filatova E. A., Filarowski A., Ozeryanskii V. A. Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 182-184.
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TY - JOUR
DO - 10.1016/j.mencom.2015.05.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.007
TI - Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives
T2 - Mendeleev Communications
AU - Kachalkina, Svetlana Gennad'evna
AU - Borodkin, Gennadii Sergeevich
AU - Pozharskii, Alexander Fedorovich
AU - Antonov, Alexander Sergeevich
AU - Borodkina, Inna Gennadievna
AU - Maltsev, Yuri Fedorovich
AU - Filatova, Ekaterina Aleksandrovna
AU - Filarowski, Aleksander
AU - Ozeryanskii, Valery Anatol'evich
PY - 2015
DA - 2015/04/28
PB - Mendeleev Communications
SP - 182-184
IS - 3
VL - 25
ER -
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@article{2015_Kachalkina,
author = {Svetlana Gennad'evna Kachalkina and Gennadii Sergeevich Borodkin and Alexander Fedorovich Pozharskii and Alexander Sergeevich Antonov and Inna Gennadievna Borodkina and Yuri Fedorovich Maltsev and Ekaterina Aleksandrovna Filatova and Aleksander Filarowski and Valery Anatol'evich Ozeryanskii},
title = {Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.007},
number = {3},
pages = {182--184},
doi = {10.1016/j.mencom.2015.05.007}
}
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Kachalkina, Svetlana Gennad'evna, et al. “Base-promoted transformation of 2-C(O)R-1,8-bis(dimethylamino)naphthalenes into benzo[g]indole derivatives.” Mendeleev Communications, vol. 25, no. 3, Apr. 2015, pp. 182-184. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.007.

Abstract

1,8-Bis(dimethylamino)naphthalenes bearing 2-positioned trifluoroacetyl or ethoxycarbonyl group on treatment with 2-lithio-1,8-bis-dimethylamino)naphthalene undergo base-promoted transformation into benzo[g]indole derivatives in small to moderate yield, representing previously unknown mode of the pyrrole ring closure which proceeds via deprotonation of the NMe group.

References

1.
10.1016/j.mencom.2015.05.007_sbref0005a
Alder
J. Chem. Soc., Chem. Commun., 1968
3.
10.1016/j.mencom.2015.05.007_bib0010
Pozharskii
The Chemistry of Anilines, 2007
4.
10.1016/j.mencom.2015.05.007_bib0015
Pozharskii
Russ. J. Org. Chem., 1996
7.
Proton sponge phosphines: electrospray-active ligands
Farrer N.J., McDonald R., McIndoe J.S.
Dalton Transactions, 2006
8.
peri-Naphthylenediamines
Pozharskii A.F., Tregub N.G., Vistorobskii N.V., Romanova E.Y., Starikova Z.A., Yanovsky A.I.
Russian Chemical Bulletin, 1999
9.
10.1016/j.mencom.2015.05.007_bib0040
Okada
Book of Abstracts. Congress of Heterocyclic Chemistry (Japan), 2003
10.
1,8,1',8'-Tetrakis(dimethylamino)-2,2'-dinaphthylmethanols: double in/out proton sponges with low-barrier hydrogen-bond switching.
Pozharskii A.F., Degtyarev A.V., Ozeryanskii V.A., Ryabtsova O.V., Starikova Z.A., Borodkin G.S.
Journal of Organic Chemistry, 2010
11.
10.1016/j.mencom.2015.05.007_sbref0050a
Sundberg
1984
12.
10.1016/j.mencom.2015.05.007_sbref0050b
Sundberg
1996
13.
10.1016/j.mencom.2015.05.007_sbref0050c
Bergman
2008
14.
Three examples of naphthalene proton sponges with extreme or unusual structural parameters. General view on factors influencing proton sponge geometry
Boiko L.Z., Sorokin V.I., Filatova E.A., Starikova Z.A., Ozeryanskii V.A., Pozharskii A.F.
Journal of Molecular Structure, 2011