154
Views
3
CrossRef citations to date
0
Altmetric
Short Communication

Synthesis of 2-phenoxyl-2-oxo-1,4,2-oxazaphosphinanes from a three component reaction

, , , ORCID Icon, &
Pages 359-366 | Received 02 Oct 2019, Accepted 29 Nov 2019, Published online: 21 Feb 2020

References

  • (a) Borch, R.-F.; Canute, G.-W. Synthesis and Antitumor Properties of Activated Cyclophosphamide Analogues. J. Med. Chem. 1991, 34, 3044–3052.; (b) Zhang, J.; Tian, Q.; Chan, S.-Y.; Li, S.-C.; Zhou, S.-F; Duan, W.; Zhu, Y.-Z. Metabolism and Transport of Oxazaphosphorines and the Clinical Implications. Drug Metab. Rev. 2005, 37, 611–703. DOI: 10.1080/03602530500364023.
  • Kukhar, V.-P.; Solodenko, V.-A. The Phosphorus Analogues of Aminocarboxylic Acids. Russ. Chem. Rev. 1987, 56, 859–896. DOI: 10.1070/RC1987v056n09ABEH003310.
  • (a) Cristau, H.-J.; Monbrun, J.; Tillard, M.; Pirat, J.-L. First Syntheses of 2-Hydrogeno-2-Oxo-1,4,2-Oxazaphosphinanes via Intramolecular Esterification. Tetrahedron Lett. 2003, 44, 3183–3186.; (b) Haji, M. Multicomponent Reactions: A Simple and Efficient Route to Heterocyclic Phosphonates. Beilstein J. Org. Chem. 2016, 12, 1269–1301. DOI: 10.3762/bjoc.12.121.
  • (a) Zhou, J.; Qiu, Y.-G.; Feng, K.-S.; Chen, R.-Y. Studies on Cyclic α-Aminoalkanephosphonate Compounds: A Novel Synthesis of 2-Phenyl-1,4,2-Benzoxaza (or Diaza)Phosphorin 2-Oxides. Synthesis 1999, 1999, 40–42.; (b) Wang, B.; Miao, Z.-W.; Chen, R.-Y. A Simple and Convenient Procedure for the Synthesis of Naphthoquinone Fused Cyclic α-Aminophosphoryl Chloride. Heteroatom Chem. 2007, 18, 359–362. DOI: 10.1002/hc.20306; (c) Fǎgǎdar-Cosma, E.; Laichici, M.; Fǎgǎdar-Cosma, G.; Vlascici, D. Synthesis, Characterization and Correlative Biological Effects in Wheat of a Benzoxaza-and a Diaza-Phosphorus (V) Heterocycles. J. Serb. Chem. Soc. 2006, 71, 1031–1038. DOI: 10.2298/JSC0610031F; (d) Fagadar-Cosma, E., Rotaru, D., Soimu, P., Ostopovici, L., Fagadar-Cosma, G., Badea, V., Csunderlik, C. The Study of the Chemical Properties of the Alkyl and Aryldichlorophosphines. I. New Heterocyclic Compounds of Phosphorus (V)-Synthesis and Characterization. Revista de Chimie, 2002, 53, 504–507. doi:10.1055/s-1999-3676.
  • (a) Gilmore, W.-F.; Mcbride, H.-A. Synthesis of an Optically Active Alpha-Aminophosphonic Acid. J. Am. Chem. Soc. 1972, 94, 4361–4361. doi:10.1021/ja00767a065; (b) Dimukhametov, M.-N.; Bajandina, E.-V.; Davydova, E.-Y.; Dobrynin, A. B.; Gubaidullin, A. T.; Litvinov, I. A.; Alfonsov, V. A. An Alternative Reaction of Ortho-(N-benzylidene) Aminophenol With Chlorophosphites: Formation of 2-(2'-Alkoxy)-2-Oxo-3-Phenyl-5, 6-Benzo-1, 4, 2-Oxazaphosphorinanes. Mendeleev Commun. 2001, 11, 196–197. DOI: 10.1070/MC2001v011n05ABEH001478; (c) Wang, B.; Miao, Z.-W.; Huang, Y.; Chen, R.-Y. A Convenient Synthesis of 2-Alkoxy-oxo-1,4,2- oxazaphosphinanes. Heteroatom Chem. 2007, 18, 65–69. DOI: 10.1002/hc.20258; (d) Dimukhametov, M. N.; Mironov, V. F.; Mironova, E. V.; Krivolapov, D. B.; Dobrynin, A. B.; Litvinov, I. A.; Musin, R. Z. A Convenient Synthesis and Spatial Structure of 2-Aryl-2-Oxo-2-Phenylbenzo [e]-1, 4, 2-Oxazaphosphinanes. Russ. Chem. Bull. Int. Ed., 2013, 62, 1882–1891. DOI: 10.1007/s11172-013-0271-2. (e) Dimukhametov, M.; Belova, N.; Mironov, V.; Mironova, E.; Krivolapov, D.; Onys’ ko, P.; Rassukanaya, Y. Synthesis and Crystal Structure of 2-Substituted 3-Aryl-2-Oxophenylbenzo [E]-1, 4, 2-Oxazaphosphinanes. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 943–946. DOI: 10.1080/10426507.2014.993756.
  • Kraszewski, A.; Stawinski, J. H-Phosphonates: Versatile Synthetic Precursors to Biologically Active Phosphorus Compounds. Pure Appl. Chem. 2007, 79, 2217–2227. DOI: 10.1351/pac200779122217.
  • (a) Chen, X.-L.; Li, X.; Qu, L.-B.; Tang, Y.-C.; Mai, W.-P.; Wei, D.-H.; Bi, W.-Z.; Duan, L.-K.; Sun, K.; Chen, J.-Y. et al. Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-Ylphosphonates. J. Org. Chem. 2014, 79, 8407–8416.; (b) Sun, K.; Chen, X.-L.; Li, X.; Qu, L.-B.; Bi, W.-Z.; Chen, X.; Ma, H.-L.; Zhang, S.-T.; Han, B.-W.; Zhao, Y.-F. et al. H-Phosphonate-Mediated Sulfonylation of Heteroaromatic N-Oxides: A Mild and Metal-Free One-Pot Synthesis of 2-Sulfonyl Quinolines/Pyridines. Chem. Commun. 2015, 51, 12111–12114. DOI: 10.1039/C5CC04484G; (c) Bi, W.-Z.; Qu, C.; Chen, X.-L.; Qu, L.-B.; Liu, Z.-D.; Sun, K.; Li, X.; Zhao, Y.-F. A Direct C2‐Selective Phenoxylation and Alkoxylation of Quinoline N‐Oxides With Various Phenols and Alcohols in the Presence of H‐Phosphonate. Eur. J. Org. Chem. 2017, 2017, 5125–5130. DOI: 10.1002/ejoc.201701080; (d) Bi, W.-Z.; Sun, K.; Qu, C.; Chen, X.-L.; Qu, L.-B.; Zhu, S.-H.; Li, X.; Wu, H.-T.; Duan, L.-K.; Zhao, Y.-F. A Direct Metal-Free C2–H Functionalization of Quinoline N-Oxides: A Highly Selective Amination and Alkylation Strategy Towards 2-Substituted Quinolines. Org. Chem. Front. 2017, 4, 1595–1600. DOI: 10.1039/C7QO00311K.
  • Qu, Z.-B.; Chen, X.-L.; Yuan, J.-W.; Bai, Y.-L.; Chen, T.; Qu, L.-B.; Wang, F.-J.; Li, X.; Zhao, Y.-F. New Synthetic Methodology Leading to a Series of Novel Heterocyclic α-Aminophosphonates: A Very Attractive Expansion of Kabachnik-Fields Reaction. Tetrahedron 2012, 68, 3156–3159. DOI: 10.1016/j.tet.2012.02.059.
  • (a) Cherkasov, R. A.; Galkin, V. I. The Kabachnik-Fields Reaction: Synthetic Potential and the Problem of the Mechanism. Russ. Chem. Rev. 1998, 67, 857–882.; (b) Bálint, E.; Tripolszky A.; Tajti, Á. Synthesis of α-Aminophosphonates by the Kabachnik–Fields Reaction and by the Pudovik Reaction; Walter de Gruyter GmbH: Berlin, 2018; pp 108–147. DOI: 10.1070/RC1998v067n10ABEH000421.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.