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Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane. / Glukhacheva, Vera S.; Il’yasov, Sergey G.; Shestakova, Elena O. et al.

In: Materials, Vol. 15, No. 23, 8320, 12.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

Glukhacheva, VS, Il’yasov, SG, Shestakova, EO, Zhukov, EE, Il’yasov, DS, Minakova, AA, Eltsov, IV, Nefedov, AA & Genaev, AM 2022, 'Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane', Materials, vol. 15, no. 23, 8320. https://doi.org/10.3390/ma15238320

APA

Glukhacheva, V. S., Il’yasov, S. G., Shestakova, E. O., Zhukov, E. E., Il’yasov, D. S., Minakova, A. A., Eltsov, I. V., Nefedov, A. A., & Genaev, A. M. (2022). Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane. Materials, 15(23), [8320]. https://doi.org/10.3390/ma15238320

Vancouver

Glukhacheva VS, Il’yasov SG, Shestakova EO, Zhukov EE, Il’yasov DS, Minakova AA et al. Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane. Materials. 2022 Dec;15(23):8320. doi: 10.3390/ma15238320

Author

Glukhacheva, Vera S. ; Il’yasov, Sergey G. ; Shestakova, Elena O. et al. / Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane. In: Materials. 2022 ; Vol. 15, No. 23.

BibTeX

@article{1c049c9fcb3740caa7878eb779cc88d8,
title = "Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane",
abstract = "Here, we report the study results of the nitration of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) by different nitrating agents such as nitric acid, mixed nitric/sulfuric acids, nitric anhydride, and mixed concentrated nitric acid/acetic anhydride to furnish 3,7,10-trioxo-2-nitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane and 3,7,10-trioxo-2,8-dinitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane, whereas a lactam–lactim rearrangement was found to take place upon vigorous cooling to give 10-hydroxy-2,4,6,8,9,11-hexaazatricyclo[3.3.3.01,5]undec-9-ene-3,7-dione. The two competing reactions, lactam–lactim rearrangement, and nitration were found to take place. The acylation of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane was examined and the formation conditions of 2,6-di- and 2,6,9-triacetyl-substituted and 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane were established. The acetyl derivatives were found to be instable in an acidic medium and to undergo deacylation. The obtained findings correlate well with the quantum-chemical calculations.",
keywords = "acetylation, nitration, propellane, quantum-chemical predictions",
author = "Glukhacheva, {Vera S.} and Il{\textquoteright}yasov, {Sergey G.} and Shestakova, {Elena O.} and Zhukov, {Egor E.} and Il{\textquoteright}yasov, {Dmitri S.} and Minakova, {Anastasia A.} and Eltsov, {Ilia V.} and Nefedov, {Andrey A.} and Genaev, {Alexander M.}",
note = "Funding Information: The work was performed under the auspices of the Ministry of Science and Higher Education of the Russian Federation (project No. 121061500029-7) using instruments provided by the Biysk Regional Center for Shared Use of Scientific Equipment of the SB RAS (IPCET SB RAS, Biysk). Publisher Copyright: {\textcopyright} 2022 by the authors.",
year = "2022",
month = dec,
doi = "10.3390/ma15238320",
language = "English",
volume = "15",
journal = "Materials",
issn = "1996-1944",
publisher = "MDPI AG",
number = "23",

}

RIS

TY - JOUR

T1 - Synthesis of Nitro- and Acetyl Derivatives of 3,7,10-Trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane

AU - Glukhacheva, Vera S.

AU - Il’yasov, Sergey G.

AU - Shestakova, Elena O.

AU - Zhukov, Egor E.

AU - Il’yasov, Dmitri S.

AU - Minakova, Anastasia A.

AU - Eltsov, Ilia V.

AU - Nefedov, Andrey A.

AU - Genaev, Alexander M.

N1 - Funding Information: The work was performed under the auspices of the Ministry of Science and Higher Education of the Russian Federation (project No. 121061500029-7) using instruments provided by the Biysk Regional Center for Shared Use of Scientific Equipment of the SB RAS (IPCET SB RAS, Biysk). Publisher Copyright: © 2022 by the authors.

PY - 2022/12

Y1 - 2022/12

N2 - Here, we report the study results of the nitration of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) by different nitrating agents such as nitric acid, mixed nitric/sulfuric acids, nitric anhydride, and mixed concentrated nitric acid/acetic anhydride to furnish 3,7,10-trioxo-2-nitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane and 3,7,10-trioxo-2,8-dinitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane, whereas a lactam–lactim rearrangement was found to take place upon vigorous cooling to give 10-hydroxy-2,4,6,8,9,11-hexaazatricyclo[3.3.3.01,5]undec-9-ene-3,7-dione. The two competing reactions, lactam–lactim rearrangement, and nitration were found to take place. The acylation of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane was examined and the formation conditions of 2,6-di- and 2,6,9-triacetyl-substituted and 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane were established. The acetyl derivatives were found to be instable in an acidic medium and to undergo deacylation. The obtained findings correlate well with the quantum-chemical calculations.

AB - Here, we report the study results of the nitration of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane (THAP) by different nitrating agents such as nitric acid, mixed nitric/sulfuric acids, nitric anhydride, and mixed concentrated nitric acid/acetic anhydride to furnish 3,7,10-trioxo-2-nitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane and 3,7,10-trioxo-2,8-dinitro-2,4,6,8,9,11-hexaaza[3.3.3]propellane, whereas a lactam–lactim rearrangement was found to take place upon vigorous cooling to give 10-hydroxy-2,4,6,8,9,11-hexaazatricyclo[3.3.3.01,5]undec-9-ene-3,7-dione. The two competing reactions, lactam–lactim rearrangement, and nitration were found to take place. The acylation of 3,7,10-trioxo-2,4,6,8,9,11-hexaaza[3.3.3]propellane was examined and the formation conditions of 2,6-di- and 2,6,9-triacetyl-substituted and 3,7,10-trioxo-2,4,6,8,9,11-hexaacetyl-2,4,6,8,9,11-hexaaza[3.3.3]propellane were established. The acetyl derivatives were found to be instable in an acidic medium and to undergo deacylation. The obtained findings correlate well with the quantum-chemical calculations.

KW - acetylation

KW - nitration

KW - propellane

KW - quantum-chemical predictions

UR - http://www.scopus.com/inward/record.url?scp=85143803186&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/ee6a2b9f-32d5-328d-a173-00cf93c9dff0/

U2 - 10.3390/ma15238320

DO - 10.3390/ma15238320

M3 - Article

C2 - 36499831

AN - SCOPUS:85143803186

VL - 15

JO - Materials

JF - Materials

SN - 1996-1944

IS - 23

M1 - 8320

ER -

ID: 40847577