Home / Publications / Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones

Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones

Grigoriy Pavlovich Kantin 1
Grigoriy Pavlovich Kantin
, 
Mikhail Yur'evich Krasavin 1
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2017.01.031
Published 2016-12-29
Communication , Volume 27, Issue 1, 95-96
1
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kantin G. P., Krasavin M. Y. Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 95-96.
GOST all authors (up to 50) Copy
Kantin G. P., Krasavin M. Y. Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 95-96.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.01.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.031
TI - Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones
T2 - Mendeleev Communications
AU - Kantin, Grigoriy Pavlovich
AU - Krasavin, Mikhail Yur'evich
PY - 2016
DA - 2016/12/29
PB - Mendeleev Communications
SP - 95-96
IS - 1
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Kantin,
author = {Grigoriy Pavlovich Kantin and Mikhail Yur'evich Krasavin},
title = {Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones},
journal = {Mendeleev Communications},
year = {2016},
volume = {27},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.031},
number = {1},
pages = {95--96},
doi = {10.1016/j.mencom.2017.01.031}
}
MLA
Cite this
MLA Copy
Kantin, Grigoriy Pavlovich, and Mikhail Yur'evich Krasavin. “Microwave-promoted reaction of N-(alk-1-enyl)chloroacetamides with sodium azide unexpectedly yields 1H-imidazol-5(4H)-ones.” Mendeleev Communications, vol. 27, no. 1, Dec. 2016, pp. 95-96. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.031.

Abstract

A novel method to prepare biologically relevant 1H-imidazol-5(4H)-ones from aliphatic amines, isobutyraldehyde, chloroacetyl chloride and sodium azide under microwave irradiation has been developed.

References

1.
Multicomponent Reactions with Isocyanides
Dömling A., Ugi I.
Angewandte Chemie - International Edition, 2000
2.
10.1016/j.mencom.2017.01.031_bib0010
Ugi
Angew. Chem., 1959
3.
Ueber Aldehyduramide des Acetessigäthers
Biginelli P.
Berichte der deutschen chemischen Gesellschaft, 1891
4.
Condensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen
Hantzsch A.
Berichte der deutschen chemischen Gesellschaft, 1881
6.
Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds
Sharma U.K., Sharma N., Vachhani D.D., Van der Eycken E.V.
Chemical Society Reviews, 2015
7.
Multicomponent reactions of isocyanides in the synthesis of heterocycles
Ivachtchenko A.V., Ivanenkov Y.A., Kysil V.M., Krasavin M.Y., Ilyin A.P.
Russian Chemical Reviews, 2010
9.
Lewis acid-promoted 3-aza-Cope rearrangement of N-alkyl-N-allyl enamines
Cook G.R., Barta N.S., Stille J.R.
Journal of Organic Chemistry, 1992
10.
Tandem Pummerer/Mannich Cyclization Cascade of α-Sulfinylamides as a Method To Prepare Aza-Heterocycles
Padwa A., Heidelbaugh T.M., Kuethe J.T., McClure M.S., Wang Q.
Journal of Organic Chemistry, 2002
13.
Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones
Shinkevich E., Deblander J., Matthijs S., Jacobs J., De Kimpe N., Tehrani K.A.
Organic and Biomolecular Chemistry, 2011
16.
10.1016/j.mencom.2017.01.031_bib0080
Moonen
Synthesis, 2005
17.
Taking the green fluorescence out of the protein: dynamics of the isolated GFP chromophore anion
Mooney C.R., Horke D.A., Chatterley A.S., Simperler A., Fielding H.H., Verlet J.R.
Chemical Science, 2013
18.
Red-Shifted Fluorescent Aminated Derivatives of a Conformationally Locked GFP Chromophore
Baranov M.S., Solntsev K.M., Baleeva N.S., Mishin A.S., Lukyanov S.A., Lukyanov K.A., Yampolsky I.V.
Chemistry - A European Journal, 2014
19.
A G-quadruplex–containing RNA activates fluorescence in a GFP-like fluorophore
Huang H., Suslov N.B., Li N., Shelke S.A., Evans M.E., Koldobskaya Y., Rice P.A., Piccirilli J.A.
Nature Chemical Biology, 2014
20.
Fluorescent Monitoring of RNA Assembly and Processing Using the Split-Spinach Aptamer
Rogers T.A., Andrews G.E., Jaeger L., Grabow W.W.
ACS Synthetic Biology, 2014
23.
A Concise and Selective Synthesis of Novel 5-Aryloxyimidazole NNRTIs
Jones L.H., Dupont T., Mowbray C.E., Newman S.D.
Organic Letters, 2006
25.
Hydroxylation of 5H-3-Oxo-2,3,6,7,8,9-hexahydroimidazo[1,2-a]azepine derivatives by molecular oxygen
Campagna F., Carotti A., Casini G.
Journal of Heterocyclic Chemistry, 1990
26.
Facile synthesis of 4-arylidene-5-imidazolinones as synthetic analogs of fluorescent protein chromophore
Lee C., Chen Y., Lin H., Jhong Y., Chang C., Tsai C., Kao C., Chien T.
Tetrahedron, 2012
27.
López H.S., Enciso J.E., Ochoa-Terán A., Velazquez J.I., Sarmiento J.I.
Mendeleev Communications, 2016