Synthesis of Pyrimido[1,6-]quinoxalines Via Intermolecular Trapping of Thermally Generated Acyl(quinoxalin-2-yl)ketenes by Schiff Bases

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2018 Aug 17

PMID 30112078

Citations 2

Authors

Svetlana O Kasatkina

Ekaterina E Stepanova

Maksim V Dmitriev

Ivan G Mokrushin

Andrey N Maslivets

Affiliations

Soon will be listed here.

Abstract

Acyl(quinoxalin-2-yl)ketenes generated by thermal decarbonylation of 3-acylpyrrolo[1,2-]quinoxaline-1,2,4(5)-triones react regioselectively with Schiff bases under solvent-free conditions to form pyrimido[1,6-]quinoxaline derivatives in good yields.

Citing Articles

A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4 + 1] annulation reaction of fused 1-pyrrole-2,3-diones with diazooxindoles.

Topanov P, Maslivets A, Dmitriev M, Mashevskaya I, Shklyaev Y, Maslivets A Beilstein J Org Chem. 2022; 18:1532-1538.

PMID: 36447521 PMC: 9663967. DOI: 10.3762/bjoc.18.162.

Cycloaddition of 4-Acyl-1-pyrrole-2,3-diones Fused at []-Side and Cyanamides: Divergent Approach to 4-1,3-Oxazines.

Khramtsova E, Krainov A, Dmitriev M, Maslivets A Molecules. 2022; 27(16).

PMID: 36014497 PMC: 9414543. DOI: 10.3390/molecules27165257.

References

Hayes D, Mosher T, Greenshaw A . Differential effects of 5-HT2C receptor activation by WAY 161503 on nicotine-induced place conditioning and locomotor activity in rats. Behav Brain Res. 2008; 197(2):323-30. DOI: 10.1016/j.bbr.2008.08.034. View

Leber S, Kollenz G, Wentrup C . Synthesis of functionalized macrocyclic derivatives of trioxabicyclo[3.3.0]nonadiene. Beilstein J Org Chem. 2012; 8:738-43. PMC: 3388861. DOI: 10.3762/bjoc.8.83. View

Luo X, Chenard E, Martens P, Cheng Y, Tomaszewski M . Practical synthesis of quinoxalinones via palladium-catalyzed intramolecular N-arylations. Org Lett. 2010; 12(16):3574-7. DOI: 10.1021/ol101454x. View

Ma Y, Luo W, Camplo M, Liu Z, Hider R . Novel iron-specific fluorescent probes. Bioorg Med Chem Lett. 2005; 15(14):3450-2. DOI: 10.1016/j.bmcl.2005.05.010. View

Liu R, Huang Z, Murray M, Guo X, Liu G . Quinoxalin-2(1H)-one derivatives as inhibitors against hepatitis C virus. J Med Chem. 2011; 54(16):5747-68. DOI: 10.1021/jm200394x. View

Xu Z, de Moliner F, Cappelli A, Hulme C . Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry. Org Lett. 2013; 15(11):2738-41. PMC: 3727662. DOI: 10.1021/ol401068u. View

Miyashiro J, Woods K, Park C, Liu X, Shi Y, Johnson E . Synthesis and SAR of novel tricyclic quinoxalinone inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1). Bioorg Med Chem Lett. 2009; 19(15):4050-4. DOI: 10.1016/j.bmcl.2009.06.016. View

Khlebnikov A, Novikov M, Pakalnis V, Iakovenko R, Yufit D . Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems. Beilstein J Org Chem. 2014; 10:784-93. PMC: 3999847. DOI: 10.3762/bjoc.10.74. View

Cookson R, Barrett T, Barrett A . β-Keto-dioxinones and β,δ-diketo-dioxinones in biomimetic resorcylate total synthesis. Acc Chem Res. 2015; 48(3):628-42. DOI: 10.1021/ar5004169. View

10.

Sawant R, Stevens M, Skold C, Odell L . Microwave-Assisted Branching Cascades: A Route to Diverse 3,4-Dihydroquinazolinone-Embedded Polyheterocyclic Scaffolds. Org Lett. 2016; 18(20):5392-5395. DOI: 10.1021/acs.orglett.6b02774. View

11.

Pereira J, Pessoa A, Cordeiro M, Fernandes R, Prudencio C, Noronha J . Quinoxaline, its derivatives and applications: A State of the Art review. Eur J Med Chem. 2014; 97:664-72. DOI: 10.1016/j.ejmech.2014.06.058. View

12.

Kollenz G, Wentrup C . From dipivaloylketene to tetraoxaadamantanes. Beilstein J Org Chem. 2018; 14:1-10. PMC: 5769086. DOI: 10.3762/bjoc.14.1. View

13.

Presset M, Coquerel Y, Rodriguez J . Periselectivity switch of acylketenes in cycloadditions with 1-azadienes: microwave-assisted diastereoselective domino three-component synthesis of α-spiro-δ-lactams. Org Lett. 2010; 12(18):4212-5. DOI: 10.1021/ol101938r. View

14.

Rosenzweig-Lipson S, Zhang J, Mazandarani H, Harrison B, Sabb A, Sabalski J . Antiobesity-like effects of the 5-HT2C receptor agonist WAY-161503. Brain Res. 2006; 1073-1074:240-51. DOI: 10.1016/j.brainres.2005.12.052. View

15.

Reber K, Tilley S, Sorensen E . Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis. Chem Soc Rev. 2009; 38(11):3022-34. PMC: 3227143. DOI: 10.1039/b912599j. View

16.

Presset M, Coquerel Y, Rodriguez J . Microwave-assisted domino and multicomponent reactions with cyclic acylketenes: expeditious syntheses of oxazinones and oxazindiones. Org Lett. 2009; 11(24):5706-9. DOI: 10.1021/ol9024056. View

17.

Tanimori S, Nishimura T, Kirihata M . Synthesis of novel quinoxaline derivatives and its cytotoxic activities. Bioorg Med Chem Lett. 2009; 19(15):4119-21. DOI: 10.1016/j.bmcl.2009.06.007. View

18.

Galvez J, Castillo J, Quiroga J, Rajzmann M, Rodriguez J, Coquerel Y . Divergent chemo-, regio-, and diastereoselective normal electron-demand Povarov-type reactions with α-oxo-ketene dienophiles. Org Lett. 2014; 16(16):4126-9. DOI: 10.1021/ol5018245. View

19.

Preciado S, Vicente-Garcia E, Llabres S, Luque F, Lavilla R . Exploration of forbidden Povarov processes as a source of unexpected reactivity: a multicomponent Mannich-Ritter transformation. Angew Chem Int Ed Engl. 2012; 51(28):6874-7. DOI: 10.1002/anie.201202927. View

20.

Tariq S, Somakala K, Amir M . Quinoxaline: An insight into the recent pharmacological advances. Eur J Med Chem. 2017; 143:542-557. DOI: 10.1016/j.ejmech.2017.11.064. View