Home / Publications / Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones

Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones

2
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Shmatova O. I., Nenajdenko V. G. Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 270-271.
GOST all authors (up to 50) Copy
Shmatova O. I., Nenajdenko V. G. Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones // Mendeleev Communications. 2018. Vol. 28. No. 3. pp. 270-271.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.05.013
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.013
TI - Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones
T2 - Mendeleev Communications
AU - Shmatova, Olga I
AU - Nenajdenko, Valentin Georgievich
PY - 2018
DA - 2018/04/27
PB - Mendeleev Communications
SP - 270-271
IS - 3
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Shmatova,
author = {Olga I Shmatova and Valentin Georgievich Nenajdenko},
title = {Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.013},
number = {3},
pages = {270--271},
doi = {10.1016/j.mencom.2018.05.013}
}
MLA
Cite this
MLA Copy
Shmatova, Olga I., and Valentin Georgievich Nenajdenko. “Synthesis of azacycloalkane-1,2-fused pyrroles via alkylation of cyclic ketimines with α-bromo ketones.” Mendeleev Communications, vol. 28, no. 3, Apr. 2018, pp. 270-271. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.05.013.

Abstract

The reaction of 2-alkyl-substituted 5-, 6- and 7-membered cyclic imines with a-bromo ketones in the presence of Hünig's base affords 2,3-dihydro-1H-pyrrolizines, 5,6,7,8-tetrahydroindolizines and 6,7,8,9-tetrahydro-5H-pyrrolo[1,2-a]azepines, respectively.

References

2.
10.1016/j.mencom.2018.05.013_sbref0005b
Gulevich
Synlett, 2009
5.
Synthesis of Tetrazole-Derived Organocatalysts via Azido-Ugi Reaction with Cyclic Ketimines
6.
Highly β‐Regioselective Friedel–Crafts Aminoalkylation of Pyrroles with Cyclic Perfluoroalkylated Imines
Shmatova O.I., Shevchenko N.E., Balenkova E.S., Röschenthaler G., Nenajdenko V.G.
European Journal of Organic Chemistry, 2013
7.
Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines
Nenajdenko V.G., Zakurdaev E.P., Prusov E.V., Balenkova E.S.
Tetrahedron, 2004
9.
Voznesenskaia N.G., Shmatova O.I., Nenajdenko V.G.
Mendeleev Communications, 2017
10.
Kutovaya I.V., Shmatova O.I., Nenajdenko V.G.
Mendeleev Communications, 2018
14.
Synthesis of 2-(3-coumarinyl)pyrrolo[2,1-a]isoquinoline derivatives by the chichibabin reaction
Kulikova Y.A., Surikova O.V., Mikhailovskii A.G., Vakhrin M.I.
Chemistry of Heterocyclic Compounds, 2011
16.
10.1016/j.mencom.2018.05.013_sbref0020e
Nair
Chem. Sect. B., 1980
18.
Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange
Ploypradith P., Jinaglueng W., Pavaro C., Ruchirawat S.
Tetrahedron Letters, 2003
19.
Novel hybrids from lamellarin D and combretastatin A 4 as cytotoxic agents
Shen L., Yang X., Yang B., He Q., Hu Y.
European Journal of Medicinal Chemistry, 2010
20.
Design and total synthesis of Mannich derivatives of marine natural product lamellarin D as cytotoxic agents
Shen L., Xie N., Yang B., Hu Y., Zhang Y.
European Journal of Medicinal Chemistry, 2014
24.
Investigations on cytotoxicity and anti-inflammatory potency of licofelone derivatives
Liu W., Zhou J., Bensdorf K., Zhang H., Liu H., Wang Y., Qian H., Zhang Y., Wellner A., Rubner G., Huang W., Guo C., Gust R.
European Journal of Medicinal Chemistry, 2011
25.
Arylpyrrolizines as Inhibitors of Microsomal Prostaglandin E2 Synthase-1 (mPGES-1) or as Dual Inhibitors of mPGES-1 and 5-Lipoxygenase (5-LOX)
Liedtke A.J., Keck P.R., Lehmann F., Koeberle A., Werz O., Laufer S.A.
Journal of Medicinal Chemistry, 2009
27.
28.
Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl)lactams. Synthesis of cyclic ketimines
Hua D.H., Miao S.W., Bharathi S.N., Katsuhira T., Bravo A.A.
Journal of Organic Chemistry, 1990
29.
A Practocal Prepraration of D1-2-Substituted and D1-2,3-Disubstituted Pyrrolines
L. Sorgi K., L. Haslego M., A. Maryanoff C., Scott L.
Heterocycles, 1993