Synthesis 2022; 54(17): 3899-3905
DOI: 10.1055/a-1504-8924
special topic
Special Issue in memory of Prof. Ferenc Fülöp

Synthesis of Cyclic Phosphinates by Microwave-Assisted Ionic-Liquid-Promoted Alcoholysis

Nikoletta Harsági
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
,
Nóra Zsuzsa Kiss
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
,
László Drahos
b   Research Centre for Natural Sciences, MS Proteomics Research Group, 1117 Budapest, Hungary
,
György Keglevich
a   Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1521 Budapest, Hungary
› Author Affiliations
This project was supported by the National Research, Development and Innovation Office (K134318). This project was also financed by the National Research, Development and Innovation Fund of Hungary in the frame of the FIEK_16-1-2016-0007 (Higher Education and Industrial Cooperation Center) project, as well as by FIKP-BIO. N.Z.K. is grateful for the János Bolyai Research Scholarship of the Hungarian Academy of Sciences (BO/00130/19/7).


Dedicated to Professor Ferenc Fülöp on the occasion of his 70th birthday

Abstract

A series of 1-alkoxy-3-methyl- and 3,4-dimethyl-3-phospholene 1-oxides, as well as 1-alkoxy-3-methylphospholane 1-oxides were prepared in good yields by the microwave (MW)-assisted [bmim][PF6]-catalyzed transesterification of the corresponding methyl or ethyl esters. The alcoholyses studied represent another case, where MW irradiation has had a crucial role on the course of the reaction. The method developed is an alternative possibility to other esterifications starting from the corresponding phosphinic chlorides and acids.

Supporting Information



Publication History

Received: 15 April 2021

Accepted after revision: 10 May 2021

Accepted Manuscript online:
10 May 2021

Article published online:
09 June 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

  • 1 Quin LD. The Heterocyclic Chemistry of Phosphorus: System Based on the Phosphorus–Carbon Bond. Wiley; New York: 1981: 368-370
  • 2 Pakulski Z, Kwiatosz R, Pietrusiewicz KM. Tetrahedron Lett. 2003; 44: 5469
  • 3 Pietrusiewicz KM, Koprowski M, Pakulski Z. Tetrahedron: Asymmetry 2002; 13: 1017
  • 4 Yamashita M, Yabui A, Suzuki K, Kato Y, Uchimura M, Iida A, Mizuno H, Ikai K, Oshikawa T, Parkanayi L, Clardy J. J. Carbohydr. Chem. 1997; 16: 499
  • 5 Yamashita M, Yabui A, Oshikawa T, Hanaya T, Yamamoto H. Heterocycles 1994; 38: 1449
  • 6 Keglevich G. Synthesis 1993; 931
  • 7 Keglevich G. Top. Heterocycl. Chem. 2009; 20: 65
  • 8 Keglevich G. Curr. Org. Chem. 2006; 10: 93
  • 9 Quin LD. A Guide to Organophosphorus Chemistry. Wiley; New York: 2000
  • 10 Keglevich G, Petneházy I, Miklós P, Almásy A, Tóth G, Tőke L, Quin LD. J. Org. Chem. 1987; 52: 3983
  • 11 Hasserodt U, Hunger K, Korte F. Tetrahedron 1963; 19: 1563
  • 12 Hunger K, Hasserodt U, Korte F. Tetrahedron 1964; 20: 1593
  • 13 Keglevich G, Brlik J, Janke F, Tőke L. Heteroat. Chem. 1990; 1: 419
  • 14 Keglevich G, Tőke L, Kovács A, Tóth G, Újszászy K. Heteroatom Chem. 1993; 4: 61
  • 15 Kiss NZ, Ludányi K, Drahos L, Keglevich G. Synth. Commun. 2009; 39: 2392
  • 16 Keglevich G, Bálint E, Kiss NZ, Jablonkai E, Hegedűs L, Grün A, Greiner I. Curr. Org. Chem. 2011; 15: 1802
  • 17 Kiss NZ, Böttger É, Drahos L, Keglevich G. Heteroat. Chem. 2013; 24: 283
  • 18 Kiss NZ, Keglevich G. Tetrahedron Lett. 2016; 57: 971
  • 19 Keglevich G, Kiss NZ, Grün A, Bálint E, Kovács T. Synthesis 2017; 49: 3069
  • 20 Jablonkai E, Milen M, Drahos L, Keglevich G. Tetrahedron Lett. 2013; 54: 5873
  • 21 Jablonkai E, Henyecz R, Milen M, Kóti J, Keglevich G. Tetrahedron 2014; 70: 8280
  • 22 Bálint E, Jablonkai E, Bálint M, Keglevich G. Heteroat. Chem. 2010; 21: 211
  • 23 Briot A, Bujard M, Gouverneur V, Nolan SP, Mioskowski C. Org. Lett. 2000; 2: 1517
  • 24 Hum G, Wooler K, Lee J, Taylor SD. Can. J. Chem. 2000; 78: 642
  • 25 Fangrui M, Milford AH. Bioresour. Technol. 1999; 70: 1
  • 26 Gashaw A, Getachew T, Teshita A. J. Forest Prod. Ind. 2015; 4: 80
  • 27 Froneman M, Modro TA. Tetrahedron Lett. 1988; 29: 3327
  • 28 Singh R, Nolan SP. Chem. Commun. 2005; 5456
  • 29 Bálint E, Tajti Á, Drahos L, Ilia G, Keglevich G. Curr. Org. Chem. 2013; 17: 555
  • 30 Tajti Á, Bálint E, Keglevich G. Curr. Org. Synth. 2016; 13: 638
  • 31 Kiss NZ, Henyecz R, Keglevich G. Molecules 2020; 25: 719
  • 32 Harsági N, Szőllősi B, Kiss NZ, Keglevich G. Green Process. Synth. 2021; 10: 1
  • 33 Harsági N, Bertha C, Kiss NZ, Henyecz R, Varga PR, Ábrányi-Balogh P, Drahos L, Keglevich G. Curr. Org. Chem. 2021; 25: 842
  • 34 Keglevich G, Kiss NZ, Mucsi Z, Körtvélyesi T. Org. Biomol. Chem. 2012; 10: 2011
  • 35 Mucsi Z, Kiss NZ, Keglevich G. RSC Adv. 2014; 4: 11948
  • 36 Garbacia S, Desai B, Lavastre O, Kappe CO. J. Org. Chem. 2003; 68: 9136
  • 37 Van der Eycken E, Appukkuttan P, De Borggraeve W, Dehaen W, Dallinger D, Kappe CO. J. Org. Chem. 2002; 67: 7904
  • 38 Obermayer D, Gutmann B, Kappe CO. Angew. Chem. Int. Ed. 2009; 48: 8321
  • 39 Leadbeater NE, Torenius HM. J. Org. Chem. 2002; 67: 3145
  • 40 Hohmann E, Keglevich G, Greiner I. Phosphorus, Sulfur Silicon Relat. Elem. 2007; 182: 2351
  • 41 Bagi P, Kállay M, Hessz D, Kubinyi M, Holczbauer T, Czugler M, Fogassy E, Keglevich G. Tetrahedron: Asymmetry 2014; 25: 318