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Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products

Mikhail Yur'evich Krasavin 1, 2
Mikhail Yur'evich Krasavin
, 
Mikhail Mikhailovich Nikulnikov 1, 2
Mikhail Mikhailovich Nikulnikov
1 Department of Organic Chemistry, Chemical Diversity Research Institute, Khimki, Moscow Region, Russian Federation
10.1016/j.mencom.2012.01.016
Published 2011-12-29
Communication , Volume 22, Issue 1, 41-42
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Krasavin M. Y., Nikulnikov M. M. Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 41-42.
GOST all authors (up to 50) Copy
Krasavin M. Y., Nikulnikov M. M. Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 41-42.
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TY - JOUR
DO - 10.1016/j.mencom.2012.01.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.016
TI - Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products
T2 - Mendeleev Communications
AU - Krasavin, Mikhail Yur'evich
AU - Nikulnikov, Mikhail Mikhailovich
PY - 2011
DA - 2011/12/29
PB - Mendeleev Communications
SP - 41-42
IS - 1
VL - 22
ER -
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@article{2011_Krasavin,
author = {Mikhail Yur'evich Krasavin and Mikhail Mikhailovich Nikulnikov},
title = {Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products},
journal = {Mendeleev Communications},
year = {2011},
volume = {22},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.016},
number = {1},
pages = {41--42},
doi = {10.1016/j.mencom.2012.01.016}
}
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Krasavin, Mikhail Yur'evich, and Mikhail Mikhailovich Nikulnikov. “Increased dipeptoid diversity resulting from post-condensational manipulation of the Ugi reaction products.” Mendeleev Communications, vol. 22, no. 1, Dec. 2011, pp. 41-42. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.016.

Keywords

acid pyrazolides
convertible isocyanid
isocyanide-based multicomponent reactions
nucleophilic opening
post-Ugi modifications

Abstract

5,6-Dihydropyrazolo[1,5-a]pyrazines prepared via the Ugi reaction involving pyrazole-3-carboxylic convertible tert-butyl isocyanide and subsequent microwave-promoted cyclization, were found to be prone to opening with primary and secondary amines, thereby providing a facile, three-step access to a greater diversity of Ugi-type dipeptoids, some of which cannot be accessed via the Ugi reaction itself.

References

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Multicomponent reactions of isocyanides in the synthesis of heterocycles
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Russian Chemical Reviews, 2010
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Imidazo[1,2-a]quinoxalines Accessed via Two Sequential Isocyanide-Based Multicomponent Reactions
Krasavin M., Shkavrov S., Parchinsky V., Bukhryakov K.
Journal of Organic Chemistry, 2009
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Proline-like β-turn mimics accessed via Ugi reaction involving monoprotected hydrazines
Krasavin M., Parchinsky V., Shumsky A., Konstantinov I., Vantskul A.
Tetrahedron Letters, 2010
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M. Nikulnikov, Ph.D. Thesis, A.N. Kosygin Moscow State Textile University, Moscow, 2010.
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M. M. Nikulnikov and M. Yu. Krasavin, Izv. Vys. Uchebn. Zaved., Khim. Khim. Tekhnol., 2010, 53 (4), 51 (in Russian).