Home / Publications / One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones

One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones

Ekaterina A Kolodina 1
Ekaterina A Kolodina
, 
Nadezhda I Lebedeva 1
Nadezhda I Lebedeva
, 
Mark Samuilovich Shvartsberg 1
Mark Samuilovich Shvartsberg
10.1016/j.mencom.2012.11.019
Published 2012-11-07
Communication , Volume 22, Issue 6, 332-333
7
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kolodina E. A., Lebedeva N. I., Shvartsberg M. S. One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 332-333.
GOST all authors (up to 50) Copy
Kolodina E. A., Lebedeva N. I., Shvartsberg M. S. One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones // Mendeleev Communications. 2012. Vol. 22. No. 6. pp. 332-333.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2012.11.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.019
TI - One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones
T2 - Mendeleev Communications
AU - Kolodina, Ekaterina A
AU - Lebedeva, Nadezhda I
AU - Shvartsberg, Mark Samuilovich
PY - 2012
DA - 2012/11/07
PB - Mendeleev Communications
SP - 332-333
IS - 6
VL - 22
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2012_Kolodina,
author = {Ekaterina A Kolodina and Nadezhda I Lebedeva and Mark Samuilovich Shvartsberg},
title = {One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones},
journal = {Mendeleev Communications},
year = {2012},
volume = {22},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.019},
number = {6},
pages = {332--333},
doi = {10.1016/j.mencom.2012.11.019}
}
MLA
Cite this
MLA Copy
Kolodina, Ekaterina A., et al. “One-Pot Synthesis of 4-Alkynyl-1-Aza-9,10-Anthraquinones from 2-Acylethynyl-3-Amino-1,4-Naphthoquinones.” Mendeleev Communications, vol. 22, no. 6, Nov. 2012, pp. 332-333. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.11.019.

Abstract

Cyclization of 2-(3-oxoalk-1-ynyl)-3-amino-1,4-naphthoquinones under the action of hydrogen bromide followed by Sonogashira cross-coupling of the thus formed 4-bromo substituted azaanthraquinone with terminal acetylenes represent the one-pot synthesis of 4-alk-1-ynyl-1-aza-9,10-anthraquinones.

References

3.
D. E. Wedge and D. G. Nagle, US Patent 6844353, 2005.
4.
R. Hargreaves, C.L. David, L. Whitesell and E. B. Skibo, Bioorg. Med. Chem. Lett., 2003, 13, 3075.
5.
J. R. Peterson, J.K. Zjawiony, S. Liu, C.D. Hufford, A.M. Clark and R. D. Rogers, J. Med. Chem., 1992, 35, 4069.
6.
Ch. Patarapanich and J. M. Cassady, J. Nat. Prod., 1999, 62, 1390.
7.
S. Mekideche and L. Desaubry, Tetrahedron Lett., 2008, 40, 5268.
8.
L. Bingjing, W. Lin, Ch. Guangying, H. Changri and W. Jing, Molecules, 2010, 15, 6349.
9.
M. S. Shvartsberg, E.A. Kolodina, N.I. Lebedeva and L. G. Fedenok, Tetrahedron Lett., 2009, 50, 6769.
10.
M. S. Shvartsberg, E.A. Kolodina, N.I. Lebedeva and L. G. Fedenok, Izv. Akad. Nauk, Ser. Khim., 2012, 580 (in Russian).
11.
Shvartsberg M.S., Kolodina E.A.
Mendeleev Communications, 2008
12.
Synthesis of benzo[g]quinoline-5,10-diones
Kolodina E.A., Lebedeva N.I., Shvartsberg M.S.
Russian Chemical Bulletin, 2007
14.
C. E. Castro, R. Holden, V.K. Honwad, A. Malte and S. Moje, J. Am. Chem. Soc., 1969, 21, 6464.