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Synthesis 2020; 52(05): 769-774
DOI: 10.1055/s-0039-1690755
DOI: 10.1055/s-0039-1690755
paper
Practical Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-phosphonic and -1-phosphinic Acids through Kabachnik–Fields and Aza-Pudovik Reaction
The authors thank the Consejo Nacional de Ciencia y Tecnología (CONACyT) for financial support through projects 286614, 807, and Cátedra contract 942, and Gobierno de Aragón-FEDER (Grupo Aminoácidos y Péptidos E19_17R; FEDER 2014-2020 ‘Construyendo Europa desde Aragón’). J.T.H.-M. also wishes to thank CONACyT for Graduate Scholarship 335029.Further Information
Publication History
Received: 20 October 2019
Accepted after revision: 07 November 2019
Publication Date:
26 November 2019 (online)
Abstract
We report here an alternative and practical method for the preparation of 1,2,3,4-tetrahydroisoquinoline-1-phosphonic acid and the first synthesis of 1,2,3,4-tetrahydroisoquinoline-1-H-phosphinic and 1,2,3,4-tetrahydroisoquinoline-1-phenylphosphinic acids through Kabachnik–Fields and aza-Pudovik reaction. This methodology does not require any metallic catalyst and proceeds under mild reaction conditions.
Key words
α-aminophosphonic acids - α-aminophosphinic acids - N-acyliminium ions - Kabachnik–Fields reaction - aza-Pudovik reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690755.
- Supporting Information
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References
- 1a Liu R, Liu L, Yang X, Fang H. Bioorg. Chem. 2019; 88: 102938
- 1b Miller EJ, Jecs E, Truax VM, Katzman BM, Tahirovic YA, Wilson RJ, Kuo KM, Kim MB, Nguyen HH, Saindane MT, Zhao H, Wang T, Sum CS, Cvijic ME, Schroeder GM, Wilson LJ, Liotta DC. J. Med. Chem. 2018; 61: 946
- 1c Kotha S, Deodhar D, Khedkar P. Org. Biomol. Chem. 2014; 12: 9054
- 1d Chrzanowska M, Grajewska A, Rozwadowska MD. Chem. Rev. 2016; 116: 12369
- 1e Martin-Liberal J, Judson I. Expert Opin. Drug Saf. 2013; 12: 905
- 1f Hatano H, Takekawa F, Hashimoto K, Ishihara M, Kawase M, Qing C, Qin-Tao W, Sakagami H. Anticancer Res. 2009; 29: 3079
- 1g Paál TA, Liljeblad A, Kanerva LT, Forró E, Fülöp F. Eur. J. Org. Chem. 2008; 5269
- 2a Van der Poorten O, Van Den Hauwe R, Eiselt E, Betti C, Guillemyn K, Chung NN, Hallé F, Bihel F, Schiller PW, Tourwé D, Sarret P, Gendron L, Ballet S. ACS Med. Chem. Lett. 2017; 8: 1177
- 2b Van der Poorten O, Knuhtsen A, Pedersen DS, Ballet S, Tourwé D. J. Med. Chem. 2016; 59: 10865
- 2c Kim KS, Zhang L, Williams D, Perez HL, Stang E, Borzilleri RM, Posy S, Lei M, Chaudhry C, Emanuel S, Talbott R. Bioorg. Med. Chem. Lett. 2014; 24: 5022
- 2d Zhang Y, Fang H, Xu W. Curr. Protein Pept. Sci. 2010; 11: 752
- 2e Örtqvist P, Peterson SD, Åkerblom E, Gossas T, Sabnis YA, Fransson R, Lindeberg G, Danielson UH, Karlén A, Sandström A. Bioorg. Med. Chem. 2007; 15: 1448
- 3a Prasad GS, Rao GN. J. Mod. Med. Chem. 2013; 1: 49
- 3b Mucha A, Kafarski P, Berlicki Ł. J. Med. Chem. 2011; 54: 5955
- 3c Orsini F, Sello G, Sisti M. Curr. Med. Chem. 2010; 17: 264
- 3d Naydenova ED, Todorov PT, Troev KD. Amino Acids 2010; 38: 23
- 3e Lejczak B, Kafarski P. Top. Heterocycl. Chem. 2009; 20: 31
- 3f Sienczyk M, Oleksyszyn J. Curr. Med. Chem. 2009; 16: 1673
- 3g Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity. Kukhar VP, Hudson HR. John Wiley & Sons; Chichester: 2000
- 4a Ordóñez M, Viveros-Ceballos JL, Romero-Estudillo I. Stereoselective Synthesis of α-Aminophosphonic Acids through Pudovik and Kabachnik-Fields Reaction. In Amino Acid - New Insights and Roles in Plant and Animal. Asao T, Asaduzzaman Md. InTech; Rijeka (Croatia): 2017. Chap. 3, 127 pp
- 4b Adbel-Rahman RM, Ali TE, Adbel-Kariem SM. ARKIVOC 2016; 183
- 4c Ordóñez M, Viveros-Ceballos JL, Cativiela C, Sayago FJ. Tetrahedron 2015; 71: 1745
- 4d Ali TE, Abdel-Kariem SM. ARKIVOC 2015; (vi): 246
- 4e Ordóñez M, Viveros-Ceballos JL, Cativiela C, Arizpe A. Curr. Org. Synth. 2012; 9: 310
- 4f Virieux D, Volle JN, Pirat JL. ARKIVOC 2012; (iv): 264
- 4g Ordóñez M, Sayago FJ, Cativiela C. Tetrahedron 2012; 68: 6369
- 4h Kudzin ZH, Kudzin MH, Drabowicz J, Stevens CV. Curr. Org. Chem. 2011; 15: 2015
- 4i Ordóñez M, Rojas-Cabrera H, Cativiela C. Tetrahedron 2009; 65: 17
- 5a Abdou MM, El-Saeed RA. Bioorg. Chem. 2019; 90: 103039
- 5b Abdou MM, O’Neill PM, Amigues E, Matziari M. Drug Discovery Today 2019; 24: 916
- 5c Ordóñez M, Viveros-Ceballos JL, Sayago FJ, Cativiela C. Synthesis 2017; 49: 987
- 5d Viveros-Ceballos JL, Ordóñez M, Sayago FJ, Cativiela C. Molecules 2016; 21: 1141
- 5e Mucha A. Molecules 2012; 17: 13530
- 6a Keglevich G, Bálint E. Molecules 2012; 17: 12821
- 6b Zefirov NS, Matveeva ED. ARKIVOC 2008; 1
- 6c Kabachnik MI, Medved TY. Dokl. Akad. Nauk SSSR 1952; 83: 689
- 6d Fields EK. J. Am. Chem. Soc. 1952; 74: 1528
- 7a Alfonsov VA. Phosphorus, Sulfur Silicon Relat. Elem. 2008; 183: 2644
- 7b Pudovik AN, Konovalova IV. Synthesis 1979; 81
- 8a Xie W, Liu N, Gong B, Ning S, Che X, Cui L, Xiang J. Eur. J. Org. Chem. 2019; 2498
- 8b Zhi Y, Ma S, Xia H, Zhang Y, Shi Z, Mu Y, Liu X. Appl. Catal., B 2019; 244: 36
- 8c Zhang R, Qin Y, Zhang L, Luo S. J. Org. Chem. 2019; 84: 2542
- 8d Lin B, Lu B, Lin R, Cui Y, Liu Y, Tang G, Zhao Y. Synlett 2018; 29: 2697
- 8e Lin B, Shi S, Lin R, Cui Y, Fang M, Tang G, Zhao Y. J. Org. Chem. 2018; 83: 6754
- 8f Chen K, Cheng Y, Chang Y, Li E, Xu Q.-L, Zhang C. Tetrahedron 2018; 74: 483
- 8g Patil MR, Dedhia NP, Kapdi AR, Kumar AV. J. Org. Chem. 2018; 83: 4477
- 8h Liang H.-P, Chen Q, Han B.-H. ACS Catal. 2018; 8: 5313
- 8i Liu Y, Wang C, Xue D, Xiao M, Li C, Xiao J. Chem. Eur. J. 2017; 23: 3051
- 8j Dhineshkumar J, Samaddar P, Prabhu KR. ACS Omega 2017; 2: 4885
- 8k Redmore D. J. Org. Chem. 1978; 43: 992
- 9 Ordóñez M, Arizpe A, Sayago FJ, Jiménez AI, Cativiela C. Molecules 2016; 21: 1140
- 10a Arguello-Velasco R, Sánchez-Muñoz GK, Viveros-Ceballos JL, Ordoñez M, Kafarski P. J. Heterocycl. Chem. 2019; 56: 2068
- 10b Viveros-Ceballos JL, Martínez-Toto EI, Eustaquio-Armenta C, Cativiela C, Ordóñez M. Eur. J. Org. Chem. 2017; 6781
- 10c Viveros-Ceballos JL, Ordóñez M, Sayago FJ, Jiménez AI, Cativiela C. Eur. J. Org. Chem. 2016; 2711
- 10d Ramírez-Marroquín OA, Romero-Estudillo I, Viveros-Ceballos JL, Cativiela C, Ordóñez M. Eur. J. Org. Chem. 2016; 308
- 10e Viveros-Ceballos JL, Sayago FJ, Ordóñez M, Cativiela C. Eur. J. Org. Chem. 2015; 1084
- 10f Bonilla-Landa I, Viveros-Ceballos JL, Ordóñez M. Tetrahedron: Asymmetry 2014; 25: 485
- 10g Arizpe A, Sayago FJ, Jiménez AI, Ordóñez M, Cativiela C. Eur. J. Org. Chem. 2011; 3074
- 11a Romero-Estudillo I, Viveros-Ceballos JL, Cazares-Carreño O, González-Morales A, Flores de Jesús B, López-Castillo M, Razo-Hernández RS, Castañeda-Corral G, Ordóñez M. Bioorg. Med. Chem. 2019; 27: 2376
- 11b Bedolla-Medrano M, Hernández-Fernández E, Ordóñez M. Synlett 2014; 25: 1145
- 11c Tibhe GD, Bedolla-Medrano M, Cativiela C, Ordóñez M. Synlett 2012; 23: 1931
- 11d Tibhe GD, Reyes-González MA, Cativiela C, Ordóñez M. J. Mex. Chem. Soc. 2012; 56: 183
- 11e Tibhe GD, Lagunas-Rivera S, Vargas-Díaz E, García-Barradas O, Ordóñez M. Eur. J. Org. Chem. 2010; 6573
- 12 Zhou M.-Y, Kong S.-S, Zhang L.-Q, Zhao M, Duan J.-A, Ou-yang Z, Wang M. Tetrahedron Lett. 2013; 54: 3962
- 13 Hu G, Chen W, Ma D, Zhang Y, Xu P, Gao Y, Zhao Y. J. Org. Chem. 2016; 81: 1704
- 14 Shinde AH, Archith N, Malipatel S, Sharada DS. Tetrahedron Lett. 2014; 55: 6821
- 15 Choudhury AR, Mukherjee S. Chem. Sci. 2016; 7: 6940
- 16 Pelletier JC, Cava MP. J. Org. Chem. 1987; 52: 616
For representative publications, see: