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Citation: HU Jiu-Rong, ZHENG Da-Gui. Efficient Synthesis and Crystal Structures of Intermediates of Benzanilide Derivatives Catalyzed by Ph3P/DDQ[J]. Chinese Journal of Inorganic Chemistry, ;2014, (2): 459-465. doi: 10.11862/CJIC.2014.010 shu

Efficient Synthesis and Crystal Structures of Intermediates of Benzanilide Derivatives Catalyzed by Ph3P/DDQ

  • 1.

    Key Laboratory of Applied Organic Chemistry, Higher Institutions of Jiangxi Province, School of Chemistry and Chemical Engineering, Shangrao Normal University, Shangrao, Jiangxi 334001, China

  • Corresponding author: HU Jiu-Rong, 
  • Received Date: 7 May 2013
    Available Online: 14 September 2013

    Fund Project:

  • Treatment of 2-substituted benzoic acids (2-isopropylbenzoic acid and salicylic acid) with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) mediated by PPh3 at room temperature produced two 1,4-disubstituted 2,3-dicyano-5,6-dichlorobenzenes (2 and 3) in good yields. Heating a chloroform solution of 2 and 3 to the reflux temperature in the presence of phenylamine generated amide derivatives 4 and 5, respectively. All the target compounds were fully characterized by elemental analysis, MSand 1H NMRspectrometry, and the structures of compounds 2 and 3 were further confirmed by single-crystal determination. 1,4-Bis(2-isopropylbenzoate)-2,3-dicyano-5,6-dichlorobenzene (2) crystallizes in monoclinic space group P21/c with cell parameters: a=1.2875(3) nm, b=1.5186(2) nm, c=1.5726(3) nm, β=122.23(3)°, V=2.6010(1) nm3, Dc=1.331 g·cm-3, Z=4, F(000)=1080, R1=0.0572, wR2=0.1260. 1,4-Bis(2-hydroxybenzoate)-2,3-dicyano-5,6-dichlorobenzene (3) crystallizes in triclinic space group P1 with cell parameters: a=0.87776(16) nm, b=1.13111(15) nm, c=1.18639(17) nm, α=69.290 (2)°, β=89.409 (3)°, γ=67.878 (2)°, V=1.0104(3) nm3, Dc=1.542 g·cm-3, Z=2, F(000)=476, R1=0.0383, wR2=0.0931. Strong π-π stacking interactions and intermolecular hydrogen bonds of the structures (2 and 3) stabilized the two intermediates. CCDC: 921957, 2; 935976, 3.
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    1. [1]

      [1] (a)Cupido T, Tulla-Puche J, Spengler J, et al. Curr. Opin. Drug Discovery Dev., 2007,10:768-783 (b)Bode J W. Curr. Opin. Drug Discovery Dev., 2006,9:765- 775 (c)Humphrey J M, Chamberlin A R. Chem. Rev., 1997,97: 2243-2246

    2. [2]

      [2] (a)Lyons T W, Sanford M S. Chem. Rev., 2010,110:1147-1169 (b)Arockiam P B, Bruneau C, Dixneuf P H. Chem. Rev., 2012,112:5879-5918 (c)Wang C M, Chen H, Wang Z F, et al. Angew. Chem. Int. Ed., 2012,51:7242-7245

    3. [3]

      [3] (a)Roughley S D, Jordan A M. J. Med. Chem., 2011,54:3451 -3479 (b)Montalbetti C A G N, Falque V. Tetrahedron, 2005,61: 10827-10852

    4. [4]

      [4] (a)Ishihara K, Ohara S, Yamamoto H. J. Org. Chem., 1996, 61:4196-4197 (b)Tang P. Org. Synth., 2005,81:262-272 (c)Charville H, Jackson D, Hodges G, et al. Chem. Commun., 2010,46:1813-1823 (d)Allen C L, Chhatwal A R, Williams J M J. Chem. Commun., 2012,48:666-668

    5. [5]

      [5] (a)Gunanathan C, Yehoshoa B D, Milstein D. Science, 2007, 317:790-792 (b)Ghosh S C, Muthaiah S, Zhang Y, et al. Adv. Synth. Catal., 2009,351:2643-2649 (c)Wang Y, Zhu D, Tang L, et al. Angew. Chem., Int. Ed., 2011,50:8917-8921 (d)Soule J F, Miyamura H, Kobayashi S. J. Am. Chem. Soc., 2011,133:18550-18553 (e)Kegns S, Mielby J, Mentzel U V, et al. Chem. Commun., 2012,48:2427-2429

    6. [6]

      [6] (a)Martinelli J R, Clark T P, Watson D A, et al. Angew. Chem., Int. Ed., 2007,46:8460-8463 (b)Brennfuhrer A, Neumann H, Beller M. Angew. Chem., Int. Ed., 2009,48:4114-4133 (c)Dang T T, Zhu Y, Ghosh S C, et al. Chem. Commun., 2012,48:1805-1807

    7. [7]

      [7] (a)Cho S H, Yoo E J, Bae I, et al. J. Am. Chem. Soc., 2005, 127:16046-16047 (b)Chen Z W, Jiang H F, Pan X Y, et al. Tetrahedron, 2011, 67:5920-5927

    8. [8]

      [8] (a)Nakagawa K, Onoue H, Minami K. Chem. Commun., 1966, 1:17-18 (b)Chang J W W, Chan P W H. Angew. Chem., Int. Ed., 2008,47:1138-1140 (c)Shie J, Fang J. J. Org. Chem., 2003,68:1158-1160 (d)Suto Y, Yamagiwa N, Torisawa Y. Tetrahedron Lett., 2008, 49:5732-5735 (e)Wang L, Fu H, Jiang Y, et al. Chem. Eur. J., 2008,14: 10722-10726 (f)Naota T, Murahashi S I. Synlett., 1991,10:693-694 (g)Chan W K, Ho C M, Wong M K, et al. J. Am. Chem. Soc., 2006,128:14796-14797

    9. [9]

      [9] (a)Charville H, Jackson D, Hodges G, et al. Chem. Commun., 2010,46:1813-1823 (b)Maki T, Ishihara K, Yamamoto H. Tetrahedron, 2007,63: 8645-8657 (c)Ishihara K, Ohara S, Yamamoto H. J. Org. Chem., 1996, 61:4196-4197 (d)Tang P. Org. Synth., 2005,81:262-272 (e)Arnold K, Davies B, Giles R L, et al. Adv. Synth. Catal., 2006,348:813-820 (f)Arnold K, Batsanov A S, Davies B, et al. Green Chem., 2008,10:124-134 (g)Al-Zoubi R M, Marion O, Hall D G. Angew. Chem., Int. Ed., 2008,47:2876-2879 (h)Marcelli T. Angew. Chem., Int. Ed., 2010,49:6840-6843 (i)Gernigon N, Al-Zoubi R M, Hall D G. J. Org. Chem., 2012,77:8386-8400 (j)Nelson P, Pelter A. J. Chem. Soc., 1965,9:5142-5144 (k)Collum D B, Chen S C, Ganem B. J. Org. Chem., 1978, 43:4393-4394

    10. [10]

      [10] (a)Starkov P, Sheppard T D. Org. Biomol. Chem., 2011,9: 1320-1323 (b)Lanigan R M, Starkov P, Sheppard T D J. Org. Chem., 2013,78:4512-4523

    11. [11]

      [11] Iranpoor N, Firouzabadi H, Nowrouzi N, et al. Tetrahedron, 2009,65:3893-3899

    12. [12]

      [12] Wang H B, Liu J, Deng Y, et al. Chem. Eur. J., 2009,15: 1499-1507

    13. [13]

      [13] Ma F F, Xie X M, Zhang L, et al. J. Org. Chem., 2012,77: 5279-5285

    14. [14]

      [14] Sheldrick G M. SHELXS-97, Program for the Solution of Crystal Structures, University of Göttingen, Germany, 1997.

    15. [15]

      [15] Sheldrick G M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.

    16. [16]

      [16] Reddy D S, Ovchinnikov Y E, Shishkin O V, et al. J. Am. Chem. Soc., 1996,118:4085-4089

    17. [17]

      [17] Esteruelas M A, Lahoz F J, Oro L A, et al. Organometallics, 1996,15:3670-3678

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