Home / Publications / An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones

An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones

Yana Yur'evna Shmoylova 1
Yana Yur'evna Shmoylova
, 
Yuri Alexandrovich Kovygin 1
Yuri Alexandrovich Kovygin
, 
Irina Vladimirovna Ledenyova 1
Irina Vladimirovna Ledenyova
, 
Mikhail Avramovich Prezent 2
Mikhail Avramovich Prezent
, 
Elena Dmitrievna Daeva 2
Elena Dmitrievna Daeva
, 
Sergey Viktorovich Baranin 2
Sergey Viktorovich Baranin
, 
Khidmet Sapharovich Shikhaliev 1
Khidmet Sapharovich Shikhaliev
10.1016/j.mencom.2021.03.039
Published 2021-03-03
Communication , Volume 31, Issue 2, 259-261
4
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Shmoylova Y. Y. et al. An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 259-261.
GOST all authors (up to 50) Copy
Shmoylova Y. Y., Kovygin Y. A., Ledenyova I. V., Prezent M. A., Daeva E. D., Baranin S. V., Shikhaliev K. S. An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 259-261.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.03.039
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.039
TI - An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones
T2 - Mendeleev Communications
AU - Shmoylova, Yana Yur'evna
AU - Kovygin, Yuri Alexandrovich
AU - Ledenyova, Irina Vladimirovna
AU - Prezent, Mikhail Avramovich
AU - Daeva, Elena Dmitrievna
AU - Baranin, Sergey Viktorovich
AU - Shikhaliev, Khidmet Sapharovich
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 259-261
IS - 2
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Shmoylova,
author = {Yana Yur'evna Shmoylova and Yuri Alexandrovich Kovygin and Irina Vladimirovna Ledenyova and Mikhail Avramovich Prezent and Elena Dmitrievna Daeva and Sergey Viktorovich Baranin and Khidmet Sapharovich Shikhaliev},
title = {An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.039},
number = {2},
pages = {259--261},
doi = {10.1016/j.mencom.2021.03.039}
}
MLA
Cite this
MLA Copy
Shmoylova, Yana Yur'evna, et al. “An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 259-261. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.039.

Keywords

N-arylitaconimides
alkyl (3-oxopiperazin-2-ylidene)acetates
microwave irradiation
pyrido[1,2-a]pyrazin-1-ones
recyclization

Abstract

New polyfunctional hydrogenated pyrido[1,2-a]pyrazin- 1-ones were obtained by regioselective recyclization of N-arylitaconimides with alkyl (3-oxopiperazin-2-ylidene)acetates. The supposed cascade reaction pathway involves the Michael addition of the nucleophile to an activated double bond and subsequent intramolecular transamidation of the intermediate with simultaneous recycling.

References

2.
B. H. Lee and M. Kalamazoo, Patent WO 94/29319, 1994.
3.
Ecteinascidins:  Putative Biosynthetic Precursors and Absolute Stereochemistry
Sakai R., Jares-Erijman E.A., Manzanares I., Silva Elipe M.V., Rinehart K.L.
Journal of the American Chemical Society, 1996
5.
Structures of marcfortine B and C (X-ray analysis), alkaloids from
Prangé T., Billion M., Vuilhorgne M., Pascard C., Polonsky J., Moreau S.
Tetrahedron Letters, 1981
6.
Antineoplastic Agents 430. Isolation and Structure of Cribrostatins 3, 4, and 5 from the Republic of Maldives Cribrochalina Species
Pettit G.R., Knight J.C., Collins J.C., Herald D.L., Pettit R.K., Boyd M.R., Young V.G.
Journal of Natural Products, 2000
9.
C. W. am Ende, J.M. Humphrey, D.S. Johnson, G.W. Kauffman, M.Y. Pettersson, D.A. Rankic, A.F. Stepan and P. R. Verhoest, Patent WO 2015/150957, 2015.
10.
C. C. Kong and B. Liu, Patent WO 2006/066414, 2006.
11.
Antiviral Characteristics of GSK1265744, an HIV Integrase Inhibitor Dosed Orally or by Long-Acting Injection
Yoshinaga T., Kobayashi M., Seki T., Miki S., Wakasa-Morimoto C., Suyama-Kagitani A., Kawauchi-Miki S., Taishi T., Kawasuji T., Johns B.A., Underwood M.R., Garvey E.P., Sato A., Fujiwara T.
Antimicrobial Agents and Chemotherapy, 2015
12.
In VitroAntiretroviral Properties of S/GSK1349572, a Next-Generation HIV Integrase Inhibitor
Kobayashi M., Yoshinaga T., Seki T., Wakasa-Morimoto C., Brown K.W., Ferris R., Foster S.A., Hazen R.J., Miki S., Suyama-Kagitani A., Kawauchi-Miki S., Taishi T., Kawasuji T., Johns B.A., Underwood M.R., et. al.
Antimicrobial Agents and Chemotherapy, 2010
14.
A novel method for the synthesis of pyrimido[1,2-a]benzimidazoles
Vandyshev D.Y., Shikhaliev K.S., Kokonova A.V., Potapov A.Y., Kolpakova M.G., Sabynin A.L., Zubkov F.I.
Chemistry of Heterocyclic Compounds, 2016
15.
10.1016/j.mencom.2021.03.039_bib0075
Vandyshev
J. Org. Chem., 2017
16.
Cascade recyclization of N-arylitaconimides as a new approach to the synthesis of polyfunctional octahydroquinolines
Kovygin Y.A., Shikhaliev K.S., Krysin M.Y., Potapov A.Y., Ledenyova I.V., Kosheleva Y.A., Vandyshev D.Y.
Chemistry of Heterocyclic Compounds, 2019
18.
Antiviral Activity of GW678248, a Novel Benzophenone Nonnucleoside Reverse Transcriptase Inhibitor
Ferris R.G., Hazen R.J., Roberts G.B., St. Clair M.H., Chan J.H., Romines K.R., Freeman G.A., Tidwell J.H., Schaller L.T., Cowan J.R., Short S.A., Weaver K.L., Selleseth D.W., Moniri K.R., Boone L.R., et. al.
Antimicrobial Agents and Chemotherapy, 2005
19.
Synthesis and biological evaluation of naphthyl phenyl ethers (NPEs) as novel nonnucleoside HIV-1 reverse transcriptase inhibitors
Gu S., Zhang X., He Q., Yang L., Ma X., Zheng Y., Yang S., Chen F.
Bioorganic and Medicinal Chemistry, 2011
20.
Synthesis of alkyl hexahydropyrazino-[1,2-c]pyrimidine-9-carboxylates
Vovk M.V., Kushnir O.V., Melˈnichenko N.V., Tsymbal I.F.
Chemistry of Heterocyclic Compounds, 2011
21.
Synthesis and thermal cyclization reactions of methyl isocrotonate derivatives.
KAWAHARA N., SHIMAMORI T., ITOH T., TAKAYANAGI H., OGURA H.
Chemical and Pharmaceutical Bulletin, 2011