Citation: Peng Wang, Rui Zhang, Jin Cai, Jun-Qing Chen, Min Ji. Efficient synthesis of functionalized 1,3-dihydroisobenzofurans from salicylaldehydes:Application to the synthesis of escitalopram[J]. Chinese Chemical Letters, ;2014, 25(4): 549-552. doi: 10.1016/j.cclet.2014.01.017 shu

Efficient synthesis of functionalized 1,3-dihydroisobenzofurans from salicylaldehydes:Application to the synthesis of escitalopram

  • Corresponding author: Min Ji, 
  • Received Date: 11 September 2013
    Available Online: 17 December 2013

    Fund Project: This work is supported by the National Basic Research Program of China (No. 2011CB933503) (No. 2011CB933503)

  • An efficient synthesis of substituted 1,3-dihydroisobenzofurans is developed. In this novel route, o-aroylbenzaldehydes, as key intermediates, can be obtained by lead tetraacetate oxidation of N-aroylhydrazones of salicylaldehydes. The mild and general strategy enables the synthesis of various substituted 1,3-dihydroisobenzofurans in high yields. Moreover, this method can be applied to efficiently synthesize escitalopram.
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    1. [1]

      [1] J.F. DeBernardis, D.L. Arendsen, J.J. Kyncl, D.J. Kerkman, Conformationally defined adrenergic agents. 4. 1-(Aminomethyl)phthalans: synthesis and pharmacological consequences of the phthalan ring oxygen atom, J. Med. Chem. 30 (1987) 178-184.

    2. [2]

      [2] Y.J. Kwon, M.J. Sohn, C.J. Kim, H. Koshino, W.G. Kim, Flavimycins A and B, dimeric 1,3-dihydroisobenzofurans with peptide deformylase inhibitory activity from Aspergillus flavipes, J. Nat. Prod. 75 (2012) 271-274.

    3. [3]

      [3] Y.J. Kwon, C.J. Zheng, W.G. Kim, Isolation and identification of FR198248, a hydroxylated 1,3-dihydroisobenzofuran, from Aspergillus flavipes as an inhibitor of peptide deformylase, Biosci. Biotechnol. Biochem. 74 (2010) 390-393.

    4. [4]

      [4] A. Zimmermann, F. Tian, H.L. de Diego, et al., Structural characterisation and dehydration behaviour of siramesine hydrochloride, J. Pharm. Sci. 98 (2009) 3596-3607.

    5. [5]

      [5] H. Kubota, M. Fujii, K. Ikeda, et al., Spiro-substituted piperidines as neurokinin receptor antagonists. I. Design and synthesis of ( )-N-[2-(3,4-dichlorophenyl)- 4-(spiro [isobenzofuran-1(3H),40piperidin]-10-yl)butyl]-N-methylbenzamide, YM-35375, as a new lead compound for novel neurokinin receptor antagonists, Chem. Pharm. Bull. 46 (1998) 351-354.

    6. [6]

      [6] N. Rao, The clinical pharmacokinetics of escitalopram, Clin. Pharmacokinet. 46 (2007) 281-290.

    7. [7]

      [7] H. Feichtiager, H. Linden, Preparation of chloro-phthalanes, US 3,176,024,1965.

    8. [8]

      [8] D.D. Phillips, S.B. Soloway, Production of substituted halogenated phthalans, US 3,036,092,1962.

    9. [9]

      [9] W.J. Houlihan, J. Nadelson, Substituted isochroman or withal an piperidenes, US 3,745,165,1973.

    10. [10]

      [10] R. Mancuso, S. Mehta, B. Gabriele, et al., A simple and mild synthesis of 1Hisochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols, J. Org. Chem. 75 (2010) 897-901.

    11. [11]

      [11] B. Gabriele, R. Mancuso, G. Salerno, A novel synthesis of 2-functionalized benzofurans by palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)- phenols followed by acid-catalyzed allylic isomerization or allylic nucleophilic substitution, J. Org. Chem. 73 (2008) 7336-7341.

    12. [12]

      [12] A. Bacchi, M. Costa, N. Della Cà, et al., Synthesis of 1-(alkoxycarbonyl)methylene- 1,3-dihydroisobenzofurans and 4-(alkoxycarbonyl)benzo[c]pyrans by palladium- catalysed oxidative carbonylation of 2-alkynylbenzyl alcohols, 2-alkynylbenzaldehydes and 2-alkynylphenyl ketones, Eur. J. Org. Chem. 2004 (2004) 574-585.

    13. [13]

      [13] N. Della Ca, F. Campanini, B. Gabriele, et al., Cascade reactions: catalytic synthesis of functionalized 1,3-dihydroisobenzofuran and tetrahydrofuran derivatives by sequential nucleophilic ring opening-heterocyclization-oxidative carbonylation of alkynyloxiranes, Adv. Synth. Catal. 351 (2009) 2423-2432.

    14. [14]

      [14] B. Gabriele, G. Salerno, A. Fazio, R. Pittelli, Versatile synthesis of (Z)-1-alkylidene- 1,3-dihydroisobenzofurans and 1H-isochromenes by palladium-catalyzed cycloisomerization of 2-alkynylbenzyl alcohols, Tetrahedron 59 (2003) 6251-6259.

    15. [15]

      [15] Z. Chai, Z.F. Xie, X.Y. Liu, G. Zhao, J.D. Wang, Tandem addition/cyclization reaction of organozinc reagents to 2-alkynyl aldehydes: highly efficient regio- and enantioselective synthesis of 1,3-dihydroisobenzofurans and tetrasubstituted furans, J. Org. Chem. 73 (2008) 2947-2950.

    16. [16]

      [16] T. Delacroix, L. Bérillon, G. Cahiez, P. Knochel, Preparation of functionalized arylmagnesium reagents bearing an o-chloromethyl group, J. Org. Chem. 65 (2000) 8108-8110.

    17. [17]

      [17] D.S. Kim, K.K. Kang, K.S. Lee, et al., Synthesis and biological properties of new 5-cyano-1,1-disubstituted phthalans for the treatment of premature ejaculation, Bull. Korean Chem. Soc. 29 (2008) 1946-1950.

    18. [18]

      [18] L. Zhang, W. Zhang, J. Liu, J. Hu, C-F bond cleavage by intramolecular SN2 reaction of alkyl fluorides with O- and N-nucleophiles, J. Org. Chem. 74 (2009) 2850-2853.

    19. [19]

      [19] M. Guiso, A. Betrow, C. Marra, The oxa-Pictet-Spengler reaction: a highlight on the different efficiency between isochroman and phthalan or homoisochroman derivative syntheses, Eur. J. Org. Chem. 2008 (2008) 1967-1976.

    20. [20]

      [20] A. Kotali, P.A. Harris, o-Diacylbenzenes in organic synthesis. A review, Org. Prep. Proced. Int. 35 (2003) 583-601.

    21. [21]

      [21] A. Kotali, Reactions of hydrazones with lead tetraacetate in organic synthesis, Curr. Org. Chem. 6 (2002) 965-985.

    22. [22]

      [22] A. Kotali, A novel and facile synthesis of tetraacylbenzenes, Tetrahedron Lett. 35 (1994) 6753-6754.

    23. [23]

      [23] A. Kotali, I.S. Lafazanis, P.A. Harris, A novel and facile synthesis of 7,8-diacylcoumarins, Tetrahedron Lett. 48 (2007) 7181-7183.

    24. [24]

      [24] A. Kotali, V.P. Papageorgiou, The chemistry of 1,3-dioximes - a brief review, Org. Prep. Proced. Int. 23 (1991) 593-610.

    25. [25]

      [25] A.J. Bigler, K.P. Bogeso, A. Toft, V. Hansen, Quantitative structure-activity-relationships in a series of selective 5-HT uptake inhibitors, Eur. J. Med. Chem. 12 (1977) 289-295.

    26. [26]

      [26] C.Y. Jin, K.G. Boldt, K.S. Rehder, G.A. Brine, Improved syntheses of N-desmethylcitalopram and N,N-didesmethylcitalopram, Synth. Commun. 37 (2007) 901-908.

    27. [27]

      [27] C.R. Elati, N. Kolla, V.T. Mathad, Response to Dancer's comments on our article "substrate modification approach to achieve efficient resolution: didesmethylcitalopram: a key intermediate for escitalopram"[Org. Process Res. Dev. 2007, 11, 289-292], Org. Process Res. Dev. 13 (2009) 34-37.

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