Propylphosphonic anhydride (T3P®) catalyzed one-pot synthesis of α-aminonitriles

Sirigireddy Sudharsan Reddy Bhoomireddy Rajendra Prasad Reddy Peddiahgari Vasu Govardhana Reddy

Citation:  Sirigireddy Sudharsan Reddy, Bhoomireddy Rajendra Prasad Reddy, Peddiahgari Vasu Govardhana Reddy. Propylphosphonic anhydride (T3P®) catalyzed one-pot synthesis of α-aminonitriles[J]. Chinese Chemical Letters, 2015, 26(6): 739-743. doi: 10.1016/j.cclet.2015.03.021 shu

Propylphosphonic anhydride (T3P®) catalyzed one-pot synthesis of α-aminonitriles

    通讯作者: Peddiahgari Vasu Govardhana Reddy,
摘要: The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P®) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.

English

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    1. [1] Y.M. Shafran, V.A. Bakulev, V.S. Mokrushin, Synthesis and properties of a-aminonitriles, Russ. Chem. Rev. 58 (1989) 148–162.[1] Y.M. Shafran, V.A. Bakulev, V.S. Mokrushin, Synthesis and properties of a-aminonitriles, Russ. Chem. Rev. 58 (1989) 148–162.

    2. [2] D.A. Martier, W.L. Owens, D. Comer, et al., Antihypertensive agents. Synthesis and biological properties of 2-amino-4-aryl-2-imidazolines, J. Med. Chem. 16 (1973)901–908.[2] D.A. Martier, W.L. Owens, D. Comer, et al., Antihypertensive agents. Synthesis and biological properties of 2-amino-4-aryl-2-imidazolines, J. Med. Chem. 16 (1973)901–908.

    3. [3] R.O. Duthaler, Recent developments in the stereoselective synthesis of a-aminonitriles, Tetrahedron 50 (1994) 1539–1650.[3] R.O. Duthaler, Recent developments in the stereoselective synthesis of a-aminonitriles, Tetrahedron 50 (1994) 1539–1650.

    4. [4] N. Baskar, C. Fortenberry, A.R. Bunce, Synthesis of aminonitriles under mild catalytic, metal-free conditions, Tetrahedron Lett. 55 (2014) 379-381.[4] N. Baskar, C. Fortenberry, A.R. Bunce, Synthesis of aminonitriles under mild catalytic, metal-free conditions, Tetrahedron Lett. 55 (2014) 379-381.

    5. [5] A. Sengupta, C. Su, C. Bao, C.T. Tai, K.P. Loh, Graphene oxide and its functionalized derivatives as carbocatalysts in the multicomponent Strecker reaction ketones, ChemCatChem 6 (2014) 2507-2511.[5] A. Sengupta, C. Su, C. Bao, C.T. Tai, K.P. Loh, Graphene oxide and its functionalized derivatives as carbocatalysts in the multicomponent Strecker reaction ketones, ChemCatChem 6 (2014) 2507-2511.

    6. [6] Y. Wen, Y. Xiong, L. Chang, et al., Chiral bisformamides as effective organocatalysts for the asymmetric one pot three component Strecker reaction, J. Org. Chem. 72 (2007) 7715-7719.[6] Y. Wen, Y. Xiong, L. Chang, et al., Chiral bisformamides as effective organocatalysts for the asymmetric one pot three component Strecker reaction, J. Org. Chem. 72 (2007) 7715-7719.

    7. [7] J. Huang, X. Liu, Y. Wen, B. Qin, X. Feng, Enantioselective Strecker reaction of phosphinoyl ketoimines catalyzed by in situ prepared chiral N,N'-dioxides, J. Org. Chem. 72 (2007) 204-208.[7] J. Huang, X. Liu, Y. Wen, B. Qin, X. Feng, Enantioselective Strecker reaction of phosphinoyl ketoimines catalyzed by in situ prepared chiral N,N'-dioxides, J. Org. Chem. 72 (2007) 204-208.

    8. [8] S.C. Pan, B. List, Catalytic asymmetric three component acyl-Strecker reaction, Org. Lett. 9 (2007) 1149-1151.[8] S.C. Pan, B. List, Catalytic asymmetric three component acyl-Strecker reaction, Org. Lett. 9 (2007) 1149-1151.

    9. [9] M. Negru, D. Schollmeyer, H. Kunz, Enantioselective Strecker reaction catalyzed by an organocatalyst lacking a hydrogen-bond donar function, Angew. Chem. Int. Ed. Engl. 46 (2007) 9339-9341.[9] M. Negru, D. Schollmeyer, H. Kunz, Enantioselective Strecker reaction catalyzed by an organocatalyst lacking a hydrogen-bond donar function, Angew. Chem. Int. Ed. Engl. 46 (2007) 9339-9341.

    10. [10] G.K.S. Prakash, T. Mathew, C. Panja, et al., Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs, Proc. Natl. Acad. Sci. U. S. A. 104 (2007) 3703-3706.[10] G.K.S. Prakash, T. Mathew, C. Panja, et al., Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs, Proc. Natl. Acad. Sci. U. S. A. 104 (2007) 3703-3706.

    11. [11] M.Z. Kassaee, H. Masrouri, F. Movahedi, Sulfamic acid functionalized magnetic Fe3O4 nanoparticles as an efficient and reusable catalyst for one pot synthesis of α-aminonitriles in water, Appl. Catal. A: Gen. 395 (2011) 28-33.[11] M.Z. Kassaee, H. Masrouri, F. Movahedi, Sulfamic acid functionalized magnetic Fe3O4 nanoparticles as an efficient and reusable catalyst for one pot synthesis of α-aminonitriles in water, Appl. Catal. A: Gen. 395 (2011) 28-33.

    12. [12] M.N. Sefat, D. Saberi, K. Niknam, Preparation of silica-based ionic liquid an efficient and recyclable catalyst for one pot synthesis of α-aminonitriles, Catal. Lett. 141 (2011) 1713-1720.[12] M.N. Sefat, D. Saberi, K. Niknam, Preparation of silica-based ionic liquid an efficient and recyclable catalyst for one pot synthesis of α-aminonitriles, Catal. Lett. 141 (2011) 1713-1720.

    13. [13] T. Rahi, M. Bagherrnejad, K. Niknam, Synthesis of α-aminonitriles using silica bonded N-propylpiperazine sulfamic acid as a recyclable catalyst, Chin. Chem. Lett. 23 (2012) 1103-1106.[13] T. Rahi, M. Bagherrnejad, K. Niknam, Synthesis of α-aminonitriles using silica bonded N-propylpiperazine sulfamic acid as a recyclable catalyst, Chin. Chem. Lett. 23 (2012) 1103-1106.

    14. [14] A.R. Hajipour, I.M. Dehbane, An efficient one pot synthesis of α-aminonitriles using ecofriendly Lewis acidic ionic liquid cholin chloride 2ZnCl2, Iran. J. Catal. 2 (2012) 147-151.[14] A.R. Hajipour, I.M. Dehbane, An efficient one pot synthesis of α-aminonitriles using ecofriendly Lewis acidic ionic liquid cholin chloride 2ZnCl2, Iran. J. Catal. 2 (2012) 147-151.

    15. [15] S. Ghasemi, M. Bagherrnejad, K. Niknam, Sulfuric acid {[3-(3silicapropyl)sulfanyl] propyl} ester as a recyclable solid acid catalyst for the synthesis of a-amino nitries, Iran. J. Catal. 3 (2013) 165-169.[15] S. Ghasemi, M. Bagherrnejad, K. Niknam, Sulfuric acid {[3-(3silicapropyl)sulfanyl] propyl} ester as a recyclable solid acid catalyst for the synthesis of a-amino nitries, Iran. J. Catal. 3 (2013) 165-169.

    16. [16] R. Warmuth, T.E. Munsch, R.A. Stalker, B. Li, A. Beatty, Enantioselective synthesis of benzocyclic a, a-dialkyl-amino acids: new insight into the solvent dependent stereoselectivity of the TMSCN addition to phenylglycinol derived imines, Tetrahedron 57 (2001) 6383-6397.[16] R. Warmuth, T.E. Munsch, R.A. Stalker, B. Li, A. Beatty, Enantioselective synthesis of benzocyclic a, a-dialkyl-amino acids: new insight into the solvent dependent stereoselectivity of the TMSCN addition to phenylglycinol derived imines, Tetrahedron 57 (2001) 6383-6397.

    17. [17] D. Enders, J.P. Shilvock, Some recent applications of a-aminonitrile chemistry, Chem. Soc. Rev. 29 (2000) 359-373.[17] D. Enders, J.P. Shilvock, Some recent applications of a-aminonitrile chemistry, Chem. Soc. Rev. 29 (2000) 359-373.

    18. [18] S. Kobayashi, H. Ishitani, Catalytic enantioselective addition to imines, Chem. Rev. 99 (1999) 1069-1094.[18] S. Kobayashi, H. Ishitani, Catalytic enantioselective addition to imines, Chem. Rev. 99 (1999) 1069-1094.

    19. [19] B.A. Bhanu Prasad, A. Bisal, V.K. Singh, Trimethylsilyl cyanide addition to aldimines and its application in the synthesis of (S)-phenylglycine methyl ester, Tetrahedron Lett. 45 (2004) 9565-9567.[19] B.A. Bhanu Prasad, A. Bisal, V.K. Singh, Trimethylsilyl cyanide addition to aldimines and its application in the synthesis of (S)-phenylglycine methyl ester, Tetrahedron Lett. 45 (2004) 9565-9567.

    20. [20] S. Harusawa, Y. Hmada, T. Shiori, Diethyl phosphorocyanidated (DEPC). A novel reagent for the classical Strecker's a-aminonitrile synthesis, Tetrahedron Lett. 20 (1979) 4663-4666.[20] S. Harusawa, Y. Hmada, T. Shiori, Diethyl phosphorocyanidated (DEPC). A novel reagent for the classical Strecker's a-aminonitrile synthesis, Tetrahedron Lett. 20 (1979) 4663-4666.

    21. [21] S. Nakamura, N. Sato, M. Sugimoto, T. Toru, A new approach to enantioselective cyanation of imines with Et3AlCN, Tetrahedron Asymmetry 15 (2004) 1513-1516.[21] S. Nakamura, N. Sato, M. Sugimoto, T. Toru, A new approach to enantioselective cyanation of imines with Et3AlCN, Tetrahedron Asymmetry 15 (2004) 1513-1516.

    22. [22] P. Vachal, E.N. Jacobsen, Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction, J. Am. Soc. 124 (2002) 10012-10014.[22] P. Vachal, E.N. Jacobsen, Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction, J. Am. Soc. 124 (2002) 10012-10014.

    23. [23] A. Baeza, C. Najera, J.M. Sansano, Solvent-free synthesis of racemic α-aminonitriles, Synthesis (2007) 1230-1234.[23] A. Baeza, C. Najera, J.M. Sansano, Solvent-free synthesis of racemic α-aminonitriles, Synthesis (2007) 1230-1234.

    24. [24] B.C. Ranu, S.S. Dey, A. Hajra, Indim trichloride catalyzed one-step synthesis of aaminonitriles by a three-component condensation of carbonyl compounds, amines and potassium cyanide, Tetrahedron 58 (2002) 2529-2532.[24] B.C. Ranu, S.S. Dey, A. Hajra, Indim trichloride catalyzed one-step synthesis of aaminonitriles by a three-component condensation of carbonyl compounds, amines and potassium cyanide, Tetrahedron 58 (2002) 2529-2532.

    25. [25] S.K. De, R.A. Gibbs, Bismuth trichloride catalyzed synthesis of α-aminonitriles, Tetrahedron Lett. 45 (2004) 7407-7408.[25] S.K. De, R.A. Gibbs, Bismuth trichloride catalyzed synthesis of α-aminonitriles, Tetrahedron Lett. 45 (2004) 7407-7408.

    26. [26] J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M. Srinivas, Montmorillonite KSF clay catalyzed one-pot synthesis of α-aminonitriles, Tetrahedron 60 (2004) 1767-1771.[26] J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M. Srinivas, Montmorillonite KSF clay catalyzed one-pot synthesis of α-aminonitriles, Tetrahedron 60 (2004) 1767-1771.

    27. [27] B. Karimi, A.A. Safari, One-pot synthesis of α-aminonitriles using a highly efficient and recyclable silica-based scandium (III) interphase catalyst, J. Organomet. Chem. 693 (2008) 2967-2970.[27] B. Karimi, A.A. Safari, One-pot synthesis of α-aminonitriles using a highly efficient and recyclable silica-based scandium (III) interphase catalyst, J. Organomet. Chem. 693 (2008) 2967-2970.

    28. [28] B.M. Reddy, B. Thirupathi, M.K.K. Patil, Highly efficient promoted zirconia solid acid catalysts of α-aminonitriles using trimethylsilyl cyanide, J. Mol. Catal. A: Chem. 307 (2009) 154-159.[28] B.M. Reddy, B. Thirupathi, M.K.K. Patil, Highly efficient promoted zirconia solid acid catalysts of α-aminonitriles using trimethylsilyl cyanide, J. Mol. Catal. A: Chem. 307 (2009) 154-159.

    29. [29] H.A. Oskooie, M.M. Heravi, A. Sadnia, F. Jannati, F.K. Behbahabi, Ferric perchloratecatalyzed one-pot synthesis of α-aminonitriles using trimethylsilylcyanide, Synth. Commun. 37 (2007) 2543-2548.[29] H.A. Oskooie, M.M. Heravi, A. Sadnia, F. Jannati, F.K. Behbahabi, Ferric perchloratecatalyzed one-pot synthesis of α-aminonitriles using trimethylsilylcyanide, Synth. Commun. 37 (2007) 2543-2548.

    30. [30] N.H. Khan, S. Agrawal, R.I. Kureshy, et al., Fe(Cp)2PF6 catalyzed efficient Strecker reactions of ketones and aldehydes under solvent-free conditions, Tetrahedron Lett. 49 (2008) 640-644.[30] N.H. Khan, S. Agrawal, R.I. Kureshy, et al., Fe(Cp)2PF6 catalyzed efficient Strecker reactions of ketones and aldehydes under solvent-free conditions, Tetrahedron Lett. 49 (2008) 640-644.

    31. [31] Z.L. Shen, S.J. Ji, T.P. Loh, Indium(III) iodide-mediated Strecker reaction in water: an efficient and environmentally friendly approach for the synthesis of α-aminonitriles via a three-component condensation, Tetrahedron 64 (2008) 8159-8163.[31] Z.L. Shen, S.J. Ji, T.P. Loh, Indium(III) iodide-mediated Strecker reaction in water: an efficient and environmentally friendly approach for the synthesis of α-aminonitriles via a three-component condensation, Tetrahedron 64 (2008) 8159-8163.

    32. [32] S.H. Wang, L.F. zhao, Z.M. Du, iodide catalyzed three-component Strecker-type synthesis of α-aminonitriles from aldehydes, amines and tributyltin cyanide, Chin. J. Chem. 24 (2006) 135-137.[32] S.H. Wang, L.F. zhao, Z.M. Du, iodide catalyzed three-component Strecker-type synthesis of α-aminonitriles from aldehydes, amines and tributyltin cyanide, Chin. J. Chem. 24 (2006) 135-137.

    33. [33] E. Rafiee, A. Azad, K5CoW12O40·3H2O: heterogeneous catalyst for the Streckertype aminative cyanation of aldehydes and ketones, Synth. Commun. 37 (2007) 1127-1132.[33] E. Rafiee, A. Azad, K5CoW12O40·3H2O: heterogeneous catalyst for the Streckertype aminative cyanation of aldehydes and ketones, Synth. Commun. 37 (2007) 1127-1132.

    34. [34] S.K. De, Vanadyl triflate as an efficient and recyclable catalyst for the synthesis of α-aminonitriles, Synth. Commun. 35 (2005) 1577-1582.[34] S.K. De, Vanadyl triflate as an efficient and recyclable catalyst for the synthesis of α-aminonitriles, Synth. Commun. 35 (2005) 1577-1582.

    35. [35] M.M. Mojtahedi, S. Abaee, T. Alishiri, Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles, Tetrahedron Lett. 50 (2009) 2322-2325.[35] M.M. Mojtahedi, S. Abaee, T. Alishiri, Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles, Tetrahedron Lett. 50 (2009) 2322-2325.

    36. [36] A. Heyderi, A. Arefi, S. Khaksar, R.K. Shiroodi, Guanidine hydrochloride: an active and simple catalyst for Strecker type reaction, J. Mol. Catal. A: Chem. 271 (2007) 142-144.[36] A. Heyderi, A. Arefi, S. Khaksar, R.K. Shiroodi, Guanidine hydrochloride: an active and simple catalyst for Strecker type reaction, J. Mol. Catal. A: Chem. 271 (2007) 142-144.

    37. [37] A. Shaabani, A. Maleki, M.R. Soudi, H. Mofakham, Xanthan sulfuric acid: a new and efficient bio-supported solid acid catalyst for the synthesis of α-aminonitriles by condensation of carbonyl compounds, amines and trimethylsilylcyanide, Catal. Commun. 10 (2009) 945-949.[37] A. Shaabani, A. Maleki, M.R. Soudi, H. Mofakham, Xanthan sulfuric acid: a new and efficient bio-supported solid acid catalyst for the synthesis of α-aminonitriles by condensation of carbonyl compounds, amines and trimethylsilylcyanide, Catal. Commun. 10 (2009) 945-949.

    38. [38] J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M. Srinivas, P. Vishnumuythy, Threecomponent coupling reactions in: a facile synthesis of α-aminonitriles, New J. Chem. 27 (2003) 462-465.[38] J.S. Yadav, B.V.S. Reddy, B. Eeshwaraiah, M. Srinivas, P. Vishnumuythy, Threecomponent coupling reactions in: a facile synthesis of α-aminonitriles, New J. Chem. 27 (2003) 462-465.

    39. [39] W.Y. Chen, J. Lu, Silica sulfuric acid catalyzed one-pot synthesis of α-aminonitriles, Synlett (2005) 2293-2296.[39] W.Y. Chen, J. Lu, Silica sulfuric acid catalyzed one-pot synthesis of α-aminonitriles, Synlett (2005) 2293-2296.

    40. [40] B. Karimi, D. Zareyee, Solvent-free three component Strecker reaction of ketones using highly recyclable and hydrophobic sulfonic acid based nanoreactors, J. Mater. Chem. 19 (2009) 8665-8670.[40] B. Karimi, D. Zareyee, Solvent-free three component Strecker reaction of ketones using highly recyclable and hydrophobic sulfonic acid based nanoreactors, J. Mater. Chem. 19 (2009) 8665-8670.

    41. [41] K. Niknam, D. Saberi, M. Nouri Sefat, Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the three-component synthesis of α-aminonitriles, Tetrahedron Lett. 51 (2010) 2959-2962.[41] K. Niknam, D. Saberi, M. Nouri Sefat, Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the three-component synthesis of α-aminonitriles, Tetrahedron Lett. 51 (2010) 2959-2962.

    42. [42] M. Desroses, M. Scobie, T. Helleday, A new concise synthesis of 2,3-dihydroquinazolin-4 (1H)-one derivatives, ChemInform 37 (2013) 3595-3597.[42] M. Desroses, M. Scobie, T. Helleday, A new concise synthesis of 2,3-dihydroquinazolin-4 (1H)-one derivatives, ChemInform 37 (2013) 3595-3597.

    43. [43] T.H. Ngo, H. Berndt, D. Lentz, H.U. Reissig, Linear and cyclic amides with a thiophene backbone: ultrasound-promoted synthesis and crystal structures, J. Org. Chem. 77 (2012) 9676-9683.[43] T.H. Ngo, H. Berndt, D. Lentz, H.U. Reissig, Linear and cyclic amides with a thiophene backbone: ultrasound-promoted synthesis and crystal structures, J. Org. Chem. 77 (2012) 9676-9683.

    44. [44] M. Milen, P.A. Balogh, A. Dancso, et al., T3P®-promoted Kabachnik-Fields reaction: an efficient synthesis of a-aminophosphates, ChemCatChem 54 (2013) 5430-5433.[44] M. Milen, P.A. Balogh, A. Dancso, et al., T3P®-promoted Kabachnik-Fields reaction: an efficient synthesis of a-aminophosphates, ChemCatChem 54 (2013) 5430-5433.

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  • 发布日期:  2015-03-28
  • 收稿日期:  2014-11-30
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