Citation: Hossein Mehrabi, Mahdi Hatami-Pour. Facile, one-pot synthesis of new phenanthridine derivatives through 1,4-dipolar cycloaddition of phenantridine, activated acetylenes, and aromatic aldehydes[J]. Chinese Chemical Letters, ;2014, 25(11): 1495-1498. doi: 10.1016/j.cclet.2014.05.024 shu

Facile, one-pot synthesis of new phenanthridine derivatives through 1,4-dipolar cycloaddition of phenantridine, activated acetylenes, and aromatic aldehydes

  • Corresponding author: Hossein Mehrabi, 
  • Received Date: 7 February 2014
    Available Online: 25 April 2014

  • A facile, one-pot synthesis of new phenanthridine derivatives by a three-component reaction between phenantridine, dialkyl acetylenedicarboxylates (DAADs), and aromatic aldehydes is described. The reaction is characterized by mild conditions, high selectivity, and tolerance to various functional groups.
    1. [1]

      [1] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.

    2. [2]

      [2] A. Dö mling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.

    3. [3]

      [3] M.A. Mironov, Design of multi-component reactions: from libraries of compounds to libraries of reactions, QSAR Comb. Sci. 25 (2006) 423-431.

    4. [4]

      [4] A. Padwa, S.K. Bur, The domino way to heterocycles, Tetrahedron 63 (2007) 5341- 5378.

    5. [5]

      [5] D. Marko, M.D. Mihovilovic, P. Stanetty, Metal-assisted multicomponent reactions involving carbon monoxide-towards heterocycle synthesis, Angew. Chem. Int. Ed. 46 (2007) 3612-3615.

    6. [6]

      [6] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidinesuccinates, Org. Lett. 3 (2001) 3495-3497.

    7. [7]

      [7] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidenesuccinates, Org. Lett. 4 (2002) 2807.

    8. [8]

      [8] V. Nair, A.R. Sreekanth, N. Abhilash, M.M. Bhadbhade, R.C. Gonnade, A novel threecomponent reaction for the diastereoselective synthesis of 2H-pyrimido[2,1- a]isoquinolines via 1,4-dipolar cycloaddition, Org. Lett. 4 (2002) 3575-3577.

    9. [9]

      [9] V. Nair, A.R. Sreekanth, A.T. Biju, N.P. Rath, The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2- and 1,4-benzoquinones: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines, Tetrahedron Lett. 44 (2003) 729-732.

    10. [10]

      [10] V. Nair, B.R. Devi, R.L. Varma, The Huisgen 1,4-dipolar cycloaddition involving isoquinoline, dimethyl butynedioate and activated styrenes: a facile synthesis of tetrahydrobenzoquinolizine derivatives, Tetrahedron Lett. 46 (2005) 5333-5335.

    11. [11]

      [11] V. Nair, C. Rajesh, A.U. Vinod, Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes, Acc. Chem. Res. 36 (2003) 899-907.

    12. [12]

      [12] V. Nair, R.S. Menon, A. Sreekanth, N. Abhilash, A.T. Biju, Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: a promising synthetic strategy, Acc. Chem. Res. 39 (2006) 520-530.

    13. [13]

      [13] M. Lei, Z.J. Zhan, W. Tian, P. Lu, One-pot, three-component synthesis of highly functionalized 1,3-oxazine derivatives from a,b-unsaturated imine, alkyne, and aldehyde, Tetrahedron 68 (2012) 3361-3367.

    14. [14]

      [14] V. Nair, S. Devipriya, E. Suresh, Efficient synthesis of [1,3]oxazino[2,3-a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline-DMAD zwitterion and carbonyl compounds, Tetrahedron Lett. 48 (2007) 3667-3670.

    15. [15]

      [15] H. Mehrabi, M.A. Hatami-Pour, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 43 (2013) 611-618.

    16. [16]

      [16] H. Mehrabi, J. Pishahang, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 44 (2014) 76-81.

    1. [1]

      [1] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.

    2. [2]

      [2] A. Dö mling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.

    3. [3]

      [3] M.A. Mironov, Design of multi-component reactions: from libraries of compounds to libraries of reactions, QSAR Comb. Sci. 25 (2006) 423-431.

    4. [4]

      [4] A. Padwa, S.K. Bur, The domino way to heterocycles, Tetrahedron 63 (2007) 5341- 5378.

    5. [5]

      [5] D. Marko, M.D. Mihovilovic, P. Stanetty, Metal-assisted multicomponent reactions involving carbon monoxide-towards heterocycle synthesis, Angew. Chem. Int. Ed. 46 (2007) 3612-3615.

    6. [6]

      [6] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidinesuccinates, Org. Lett. 3 (2001) 3495-3497.

    7. [7]

      [7] V. Nair, A.R. Sreekanth, A.U. Vinod, Novel pyridine-catalyzed reaction of dimethyl acetylenedicarboxylate with aldehydes: formal [2+2] cycloaddition leading to 2- oxo-3-benzylidenesuccinates, Org. Lett. 4 (2002) 2807.

    8. [8]

      [8] V. Nair, A.R. Sreekanth, N. Abhilash, M.M. Bhadbhade, R.C. Gonnade, A novel threecomponent reaction for the diastereoselective synthesis of 2H-pyrimido[2,1- a]isoquinolines via 1,4-dipolar cycloaddition, Org. Lett. 4 (2002) 3575-3577.

    9. [9]

      [9] V. Nair, A.R. Sreekanth, A.T. Biju, N.P. Rath, The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2- and 1,4-benzoquinones: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines, Tetrahedron Lett. 44 (2003) 729-732.

    10. [10]

      [10] V. Nair, B.R. Devi, R.L. Varma, The Huisgen 1,4-dipolar cycloaddition involving isoquinoline, dimethyl butynedioate and activated styrenes: a facile synthesis of tetrahydrobenzoquinolizine derivatives, Tetrahedron Lett. 46 (2005) 5333-5335.

    11. [11]

      [11] V. Nair, C. Rajesh, A.U. Vinod, Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes, Acc. Chem. Res. 36 (2003) 899-907.

    12. [12]

      [12] V. Nair, R.S. Menon, A. Sreekanth, N. Abhilash, A.T. Biju, Engaging zwitterions in carbon-carbon and carbon-nitrogen bond-forming reactions: a promising synthetic strategy, Acc. Chem. Res. 39 (2006) 520-530.

    13. [13]

      [13] M. Lei, Z.J. Zhan, W. Tian, P. Lu, One-pot, three-component synthesis of highly functionalized 1,3-oxazine derivatives from a,b-unsaturated imine, alkyne, and aldehyde, Tetrahedron 68 (2012) 3361-3367.

    14. [14]

      [14] V. Nair, S. Devipriya, E. Suresh, Efficient synthesis of [1,3]oxazino[2,3-a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline-DMAD zwitterion and carbonyl compounds, Tetrahedron Lett. 48 (2007) 3667-3670.

    15. [15]

      [15] H. Mehrabi, M.A. Hatami-Pour, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 43 (2013) 611-618.

    16. [16]

      [16] H. Mehrabi, J. Pishahang, Synthesis of functionalized pyrido[1,2-f]phenanthridines from phenanthridine, activated acetylenes, and arylidenemalononitriles, Synth. Commun. 44 (2014) 76-81.

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