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Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines

Ildar Rustemovich Iusupov 1
Ildar Rustemovich Iusupov
, 
Alexander Vital'evich Kurkin 1
Alexander Vital'evich Kurkin
1 Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
10.1016/j.mencom.2024.02.016
Published 2024-02-19
Communication , Volume 34, Issue 2, 209-211
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Iusupov I. R., Kurkin A. V. Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 209-211.
GOST all authors (up to 50) Copy
Iusupov I. R., Kurkin A. V. Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 209-211.
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TY - JOUR
DO - 10.1016/j.mencom.2024.02.016
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.016
TI - Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines
T2 - Mendeleev Communications
AU - Iusupov, Ildar Rustemovich
AU - Kurkin, Alexander Vital'evich
PY - 2024
DA - 2024/02/19
PB - Mendeleev Communications
SP - 209-211
IS - 2
VL - 34
ER -
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@article{2024_Iusupov,
author = {Ildar Rustemovich Iusupov and Alexander Vital'evich Kurkin},
title = {Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.016},
number = {2},
pages = {209--211},
doi = {10.1016/j.mencom.2024.02.016}
}
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Iusupov, Ildar Rustemovich, and Alexander Vital'evich Kurkin. “Stereoselective synthesis of spirocyclic derivatives of functionalized 2,3,4,7-tetrahydro-1H-azepines.” Mendeleev Communications, vol. 34, no. 2, Feb. 2024, pp. 209-211. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.016.

Keywords

1
2
3-triazole
7-azaspiro[4.6]undec-9-ene
8-azaspiro[5.6]dodec-10-ene
azepane
azepine
click chemistry.
metathesis reaction
spirocycle
stereoselective synthesis

Abstract

A simple and effective stereoselective synthesis of unique azaspirocyclic 2,3,4,7-tetrahydro-1H-azepine derivatives, namely, 7-azaspiro[4.6]undec-9-ene and 8-azaspiro[5.6]- dodec-10-ene, from simple commercially available reagents was accomplished. Their key 1,2-epoxy derivatives as individual diastereomers were obtained in nine steps with 31-32% overall yields. The possibility of synthesizing a library of small spiroheterocyclic molecules was exemplified by the N-Boc-protected (1RS,2SR,6RS)-1,2-epoxy-8-aza- spiro[5.6]dodec-10-ene scaffold through simple chemical modifications of its epoxide function.

References

.
The use of spirocyclic scaffolds in drug discovery
Zheng Y., Tice C.M., Singh S.B.
Bioorganic and Medicinal Chemistry Letters, 2014
.
The utilization of spirocyclic scaffolds in novel drug discovery
Zheng Y., Tice C.M.
Expert Opinion on Drug Discovery, 2016
.
Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success
Lovering F., Bikker J., Humblet C.
Journal of Medicinal Chemistry, 2009
.
New and unusual scaffolds in medicinal chemistry
Marson C.M.
Chemical Society Reviews, 2011
.
Two‐ and Three‐dimensional Rings in Drugs
Aldeghi M., Malhotra S., Selwood D.L., Chan A.W.
Chemical Biology and Drug Design, 2014
.
What Do Medicinal Chemists Actually Make? A 50-Year Retrospective
Walters W.P., Green J., Weiss J.R., Murcko M.A.
Journal of Medicinal Chemistry, 2011
.
Clicking 3′-Azidothymidine into Novel Potent Inhibitors of Human Immunodeficiency Virus
Sirivolu V.R., Vernekar S.K., Ilina T., Myshakina N.S., Parniak M.A., Wang Z.
Journal of Medicinal Chemistry, 2013
.
Concepts and Core Principles of Fragment-Based Drug Design
Kirsch P., Hartman A.M., Hirsch A.K., Empting M.
Molecules, 2019
.
Highly Selective Dopamine D3 Receptor Antagonists with Arylated Diazaspiro Alkane Cores
Reilly S.W., Griffin S., Taylor M., Sahlholm K., Weng C., Xu K., Jacome D.A., Luedtke R.R., Mach R.H.
Journal of Medicinal Chemistry, 2017
.
Structural Insights on Fragment Binding Mode Conservation
Drwal M.N., Bret G., Perez C., Jacquemard C., Desaphy J., Kellenberger E.
Journal of Medicinal Chemistry, 2018
.
Discovery of Novel Plasmodium falciparum HDAC1 Inhibitors with Dual-Stage Antimalarial Potency and Improved Safety Based on the Clinical Anticancer Drug Candidate Quisinostat
Li R., Ling D., Tang T., Huang Z., Wang M., Ding Y., Liu T., Wei H., Xu W., Mao F., Zhu J., Li X., Jiang L., Li J.
Journal of Medicinal Chemistry, 2021
.
Catalytic ring-closing metathesis of functionalized dienes by a ruthenium carbene complex
Fu G.C., Nguyen S.T., Grubbs R.H.
Journal of the American Chemical Society, 1993
.
Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs
de Lourdes G. Ferreira M., Pinheiro L.C., Santos-Filho O.A., Peçanha M.D., Sacramento C.Q., Machado V., Ferreira V.F., Souza T.M., Boechat N.
Medicinal Chemistry Research, 2013
.
(1RS,2RS,6RS)-2-(6-Amino-9H-purin-9-yl)-8-azaspiro[5.6]dodec-10-en-1-ol Dihydrochloride
Iusupov I.R., Lyssenko K.A., Altieri A., Kurkin A.V.
MolBank, 2022
.
Molecular design and biological activity of potent and selective protein kinase inhibitors related to balanol.
Koide K., Bunnage M.E., Gomez Paloma L., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C.
Chemistry & Biology, 1995
.
Enantioselective Total Syntheses of (-)-Isonitramine, (-)-Sibirine, and (+)-Nitramine by Ring-Closing Metathesis
Pandey G., Prasanna Kumara C., Kumar Burugu S., Puranik V.G.
European Journal of Organic Chemistry, 2011
.
Imino Glycals via Ruthenium-Catalyzed RCM and Isomerization
Schmidt B., Hauke S., Mühlenberg N.
Synthesis, 2014
.
Galanthamine, a Natural Product for the Treatment of Alzheimers Disease
Marco L., Carreiras M.
Recent Patents on CNS Drug Discovery, 2006