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1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines

Evgeny Gennadievich Chupakhin 1, 2
Evgeny Gennadievich Chupakhin
, 
Olga Yurievna Bakulina 1
Olga Yurievna Bakulina
, 
Dmitry Viktorovich Dar’in 1
Dmitry Viktorovich Dar’in
, 
Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
10.1016/j.mencom.2019.05.016
Published 2019-04-26
Communication , Volume 29, Issue 3, 292-293
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Chupakhin E. G. et al. 1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 292-293.
GOST all authors (up to 50) Copy
Chupakhin E. G., Bakulina O. Y., Dar’in D. V., Krasavin M. Y. 1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines // Mendeleev Communications. 2019. Vol. 29. No. 3. pp. 292-293.
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TY - JOUR
DO - 10.1016/j.mencom.2019.05.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.016
TI - 1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines
T2 - Mendeleev Communications
AU - Chupakhin, Evgeny Gennadievich
AU - Bakulina, Olga Yurievna
AU - Dar’in, Dmitry Viktorovich
AU - Krasavin, Mikhail Yur'evich
PY - 2019
DA - 2019/04/26
PB - Mendeleev Communications
SP - 292-293
IS - 3
VL - 29
ER -
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@article{2019_Chupakhin,
author = {Evgeny Gennadievich Chupakhin and Olga Yurievna Bakulina and Dmitry Viktorovich Dar’in and Mikhail Yur'evich Krasavin},
title = {1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.016},
number = {3},
pages = {292--293},
doi = {10.1016/j.mencom.2019.05.016}
}
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Chupakhin, Evgeny Gennadievich, et al. “1,1′-Carbonyldiimidazole as a cyclodehydrating agent for the Castagnoli–Cushman reaction of dicarboxylic acids and imines.” Mendeleev Communications, vol. 29, no. 3, Apr. 2019, pp. 292-293. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.05.016.

Abstract

A novel protocol for the Castagnoli–Cushman reaction of dicarboxylic acids and imines comprises the use of 1,1′-carbonyldiimidazole as the cyclodehydrating agent to in situ produce the intermediate anhydrides. In contrast to previously developed procedure involving the use of acetic anhydride, the current protocol allows one to utilize substrates prone to acylation or acid-promoted transformations, which significantly broadens the reaction scope of lactams to be obtained.

References

2.
New Heterocyclic Product Space for the Castagnoli–Cushman Three-Component Reaction
Dar’in D., Bakulina O., Chizhova M., Krasavin M.
Organic Letters, 2015
3.
Skeletal Diversity in Combinatorial Fashion: A New Format for the Castagnoli–Cushman Reaction
Lepikhina A., Dar’in D., Bakulina O., Chupakhin E., Krasavin M.
ACS Combinatorial Science, 2017
4.
Beyond the Five and Six: Evaluation of Seven-Membered Cyclic Anhydrides in the Castagnoli–Cushman Reaction
Adamovskyi M.I., Ryabukhin S.V., Sibgatulin D.A., Rusanov E., Grygorenko O.O.
Organic Letters, 2016
7.
Cyclic Anhydrides in Formal Cycloadditions and Multicomponent Reactions
González-López M., Shaw J.T.
Chemical Reviews, 2009
8.
Synthese von Carbonsäureanhydriden nach der Imidazolidmethode
Staab H.A., Walther G., Rohr W.
Chemische Berichte, 1962
9.
Practical enantioselective synthesis of a homotyrosine derivative and (R,R)-4-propyl-9-hydroxynaphthoxazine, a potent dopamine agonist
Melillo D.G., Larsen R.D., Mathre D.J., Shukis W.F., Wood A.W., Colleluori J.R.
Journal of Organic Chemistry, 1987
10.
Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride
Kantin G., Chupakhin E., Dar'in D., Krasavin M.
Tetrahedron Letters, 2017
11.
Thiolesters of Perfluorocarboxylic Acids
Hauptschein M., Stokes C.S., Nodiff E.A.
Journal of the American Chemical Society, 1952
12.
ACTION OF THIONYL CHLORIDE ON ORGANIC ACIDS1
McMaster L., Ahmann F.F.
Journal of the American Chemical Society, 1928
13.
Syntheses in the Phenanthrene and Triphenylene Series
Fieser L.F., Daudt W.H.
Journal of the American Chemical Society, 1941
15.
Enantiospecific synthesis of the trans-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazoles
Harfenist M., Hoerr D.C., Crouch R.
Journal of Organic Chemistry, 1985
17.
10.1016/j.mencom.2019.05.016_bib0085
Parvin
Lett. Org. Chem., 2017
20.
Trans-Stereoselectivity in the Reaction between Homophthalic Anhydride and Imines
Vara Y., Bello T., Aldaba E., Arrieta A., Pizarro J.L., Arriortua M.I., Lopez X., Cossío F.P.
Organic Letters, 2008