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Synthesis 2010(22): 3899-3905  
DOI: 10.1055/s-0030-1258239
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Lewis Acid Catalyzed One-Pot Selective Synthesis of Aminobenzofurans and N-Alkyl-2-aryl-2-(arylimino)acetamides: Product Dependence on the Nature of the Aniline

Sudipta Mitra, Sandip K. Hota, Partha Chattopadhyay*
Department of Chemistry, Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India
Fax: +91(33)24735197; e-Mail: partha@iicb.res.in;
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Publication History

Received 21 July 2010
Publication Date:
01 September 2010 (online)

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Abstract

An efficient one-pot reaction between isocyanides, anilines, and salicylaldehydes (2-hydroxybenzaldehydes) in the presence of a Lewis acid proceeds smoothly at room temperature within a short time interval to afford aminobenzofurans and N-alkyl-2-aryl-2-(arylimino)acetamide derivatives in high yields depending on the electron density of the aniline component.

Key words

multicomponent reaction - Lewis acids - substituent effects - cyclization - Schiff bases

    References

  • 1a Bienayme H. Hulme C. Oddon G. Schmitt P. Chem. Eur. J.  2000,  6:  3321 
    Search in Google Scholar
  • 1b Simon C. Constantieux T. Rodriguez J. Eur. J. Org. Chem.  2004,  24:  4957 
    Search in Google Scholar
  • 1c Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
  • 1d Liang B. Wang X. Wang J.-X. Du Z. Tetrahedron  2007,  63:  1981 
    Search in Google Scholar
  • 1e Syamala M. Org. Prep. Proced. Int.  2009,  41:  1 
    Search in Google Scholar
  • 1f Sun J. Xia E.-Y. Zhang l.-L. Yan C.-G. Eur. J. Org. Chem.  2009,  5247 
  • 1g Karmakar B. Banerji J. Tetrahedron Lett.  2010,  51:  2748 
    Search in Google Scholar
  • 1h Gérard S. Renzetti A. Lefevre B. Fontana A. de Maria P. Sapi J. Tetrahedron  2010,  66:  3065 
    Search in Google Scholar
  • 1i Song W. Lu W. Wang J. Lu P. Wang Y. J. Org. Chem.  2010,  75:  3481 
    Search in Google Scholar
  • 2a Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Search in Google Scholar
  • 2b Nair V. Rajesh C. Vinod AU. Bindu S. Sreekanth AR. Mathen JS. Balagopal L. Acc. Chem. Res.  2003,  36:  899 
    Search in Google Scholar
  • 2c Dömling A. Chem. Rev.  2006,  106:  17 
    Search in Google Scholar
  • 2d Teimouri MB. Mansouri F. J. Comb. Chem.  2008,  10:  507 
    Search in Google Scholar
  • 2e Li J. Liu Y. Li C. Jia X. Tetrahedron Lett.  2009,  50:  6502 
    Search in Google Scholar
  • 2f García-González MC. González-Zamora E. Santillan R. Domínguez O. Méndez-Stivalet JM. Farfán N. Tetrahedron  2009,  65:  5337 
    Search in Google Scholar
  • 2g Ramazani A. Mahyari AT. Rouhani M. Rezaei A. Tetrahedron Lett.  2009,  50:  5625 
    Search in Google Scholar
  • 2h Adib M. Mahdavi M. Bagherzadeh S. Zhu L.-G. Rahimi-Nasrabadi M. Tetrahedron Lett.  2010,  51:  27 
    Search in Google Scholar
  • 2i Kobayashi K. Shirai Y. Fukamachi S. Konishi H. Synthesis  2010,  666 
  • 3a Passerini M. Gazz. Chim. Ital.  1921,  51:  126 
    Search in Google Scholar
  • 3b Passerini M. Gazz. Chim. Ital.  1921,  51:  181 
    Search in Google Scholar
  • 4a Ugi I. Meyr R. Fetzer U. Steinbrückner C. Angew. Chem.  1959,  71:  386 
    Search in Google Scholar
  • 4b Ugi I. Steinbrückner C. Angew. Chem.  1960,  72:  267 
    Search in Google Scholar
  • 4c Ugi I. Steinbrückner C. Chem. Ber.  1961,  94:  2802 
    Search in Google Scholar
  • 4d Ugi I. Angew. Chem., Int. Ed. Engl.  1982,  21:  810 
    Search in Google Scholar
  • 4e Ugi I. Lohberger S. Karl R. In Comprehensive Organic Synthesis   Vol. 2:  Trost BM. Fleming I. Pergamon; Oxford: 1993.  Chap. 4.6. p.1083 
    Search in Google Scholar
  • 4f De Silva RA. Santra S. Andreana PR. Org. Lett.  2008,  10:  4541 
    Search in Google Scholar
  • 4g Faggi C. García-Valverde M. Marcaccini S. Menchi G. Org. Lett.  2010,  12:  788 
    Search in Google Scholar
  • 5a Ugi I. Isonitrile Chemistry   Academic Press; London: 1971. 
  • 5b Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Search in Google Scholar
  • 5c Dömling A. Chem. Rev.  2006,  106:  17 
    Search in Google Scholar
  • 6a Varala R. Nuvula S. Adapa SR. Synlett  2006,  1549 
  • 6b More SV. Sastry MNV. Yao CF. Green Chem.  2006,  8:  91 
    Search in Google Scholar
  • 6c Varala R. Enugala R. Nuvula S. Adapa SR. Synlett  2006,  1009 
  • 6d Nair V. Deepthi A. Chem. Rev.  2007,  107:  1862 
    Search in Google Scholar
  • 6e Nair V. Deepthi A. Tetrahedron  2009,  65:  10745 
    Search in Google Scholar
  • 6f Casey BM. Eakin CA. Jiao J. Sadasivam DV. Flowers RA. Tetrahedron  2009,  65:  10762 
    Search in Google Scholar
  • 6g Kidwai M. Bhatnagar D. Tetrahedron Lett.  2010,  51:  2700 
    Search in Google Scholar
  • 6h Alcaide B. Almendros P. Carrascosa R. Rosario Torres M. Eur. J. Org. Chem.  2010,  823 
  • 6i Sridharan V. Menéndez JC. Chem. Rev.  2010,  110:  3805 
    Search in Google Scholar
  • 7a Kamthong B. Robertson A. J. Chem. Soc.  1939,  925 
  • 7b Emerson OH. Bickoff EM. J. Am. Chem. Soc.  1958,  80:  4381 
    Search in Google Scholar
  • 7c DeGraw J. Bonner WA. J. Org. Chem.  1962,  27:  3917 
    Search in Google Scholar
  • 7d Stevenson PC. Veitch NC. Phytochemistry  1998,  48:  947 
    Search in Google Scholar
  • 7e Okamoto Y. Ojika M. Sakagami Y. Tetrahedron Lett.  1999,  40:  507 
    Search in Google Scholar
  • 7f Ito J. Takaya Y. Oshima Y. Niwa M. Tetrahedron  1999,  55:  2529 
    Search in Google Scholar
  • 7g Wang Y. Zhang A. Tetrahedron  2009,  65:  6986 
    Search in Google Scholar
  • 7h Rao MLN. Awasthi DK. Banerjee D. Tetrahedron Lett.  2010,  51:  1979 
    Search in Google Scholar
  • 8a Chen Y. Chen S. Lu X. Cheng H. Ou Y. Cheng H. Zhou G.-C. Bioorg. Med. Chem. Lett.  2009,  19:  1851 
    Search in Google Scholar
  • 8b Asoh K. Kohchi M. Hyoudoh I. Ohtsuka T. Masubuchi M. Kawasaki K. Ebiike H. Shiratori Y. Fukami TA. Kondoh O. Tsukaguchi T. Ishii N. Aoki Y. Shimma N. Sakaitani M. Bioorg. Med. Chem. Lett.  2009,  19:  1753 
    Search in Google Scholar
  • 8c Galal SA. Abd El-All AS. Abdallah MM. El-Diwani HI. Bioorg. Med. Chem. Lett.  2009,  19:  2420 
    Search in Google Scholar
  • 8d Abdel-Wahab BF. Abdel-Aziz HA. Ahmed EM. Eur. J. Med. Chem.  2009,  44:  2632 
    Search in Google Scholar
  • 8e Bursavich MG. Brooijmans N. Feldberg L. Hollander I. Kim S. Lombardi S. Park K. Mallon R. Gilbert AM. Bioorg. Med. Chem. Lett.  2010,  20:  2586 
    Search in Google Scholar
  • 9a Koca M. Servi S. Kirilmis C. Ahmedzade M. Kazaz C. Özbek B. Ötük G. Eur. J. Med. Chem.  2005,  40:  1351 
    Search in Google Scholar
  • 9b Schultz DM. Prescher JA. Kidd S. Marona-Lewicka D. Nichols DE. Monte A. Bioorg. Med. Chem.  2008,  16:  6242 
    Search in Google Scholar
  • 9c Ettaoussi M. Péres B. Klupsch F. Delagrange P. Boutin J.-A. Renard P. Caignard D.-H. Chavatte P. Berthelot P. Lesieur D. Yous S. Bioorg. Med. Chem.  2008,  16:  4954 
    Search in Google Scholar
  • 9d Ando K. Kawamura Y. Akai Y. Kunitomo J. Yokomizo T. Yamashita M. Ohta S. Ohishi T. Ohishi Y. Org. Biomol. Chem.  2008,  6:  296 
    Search in Google Scholar
  • 9e Kirilmis C. Ahmedzade M. Servi S. Koca M. Kizirgil A. Kazaz C. Eur. J. Med. Chem.  2008,  43:  300 
    Search in Google Scholar
  • 10a Eidamshaus C. Burch JD. Org. Lett.  2008,  10:  4211 
    Search in Google Scholar
  • 10b Gill GS. Grobelny DW. Chaplin JH. Flynn BL. J. Org. Chem.  2008,  73:  1131 
    Search in Google Scholar
  • 10c Rao Lingam VSP. Vinodkumar R. Mukkanti K. Thomas A. Gopalan B. Tetrahedron Lett.  2008,  49:  4260 
    Search in Google Scholar
  • 10d Csékei M. Novák Z. Kotschy A. Tetrahedron  2008,  64:  8992 
    Search in Google Scholar
  • 10e Isono N. Lautens M. Org. Lett.  2009,  11:  1329 
    Search in Google Scholar
  • 10f Martinez C. Alvarez R. Aurrecoechea JM. Org. Lett.  2009,  11:  1083 
    Search in Google Scholar
  • 10g Majumdar KC. Chattopadhyay B. Maji PK. Chattopadhyay SK. Samanta S. Heterocycles  2010,  81:  517 ; and references cited therein
    Search in Google Scholar
  • 11a Shen Z. Dong VM. Angew. Chem. Int. Ed.  2009,  48:  784 
    Search in Google Scholar
  • 11b Murai M. Miki K. Ohe K. Chem. Commun.  2009,  3466 
  • 11c Miyata O. Takeda N. Naito T. Heterocycles  2009,  78:  843 
    Search in Google Scholar
  • 11d János F. András K. Synthesis  2009,  85 
  • 11e Hung NT. Hussain M. Malik I. Villinger A. Langer P. Tetrahedron Lett.  2010,  51:  2420 
    Search in Google Scholar
  • 11f Kokubo K. Harada K. Mochizuki E. Oshima T. Tetrahedron Lett.  2010,  51:  955 
    Search in Google Scholar
  • 11g Bochicchio A. Chiummiento L. Funicello M. Lopardo MT. Lupattelli P. Tetrahedron Lett.  2010,  51:  2824 
    Search in Google Scholar
  • 11h Barange DK. Raju BR. Kavala V. Kuo C.-W. Tu Y.-C. Yao C.-F. Tetrahedron  2010,  66:  3754 
    Search in Google Scholar
  • 11i Jaseer EA. Prasad DJC. Sekar G. Tetrahedron  2010,  66:  2077 
    Search in Google Scholar
  • 13 Yavari I. Djahaniani H. Tetrahedron Lett.  2006,  47:  1477 
    CrossrefSearch in Google Scholar
  • 14a Program for solution of crystal structures: Sheldrick GM. SHELXS-97   University of Göttingen; Germany: 1997. 
  • 14b Sheldrick GM. Acta Crystallogr., Sect. A  1990,  46:  467 
    Search in Google Scholar
  • 15 Program for refinement of crystal structures: Sheldrick GM. SHELXL-97   University of Göttingen; Germany: 1997. 
12

Crystal data of compound 10a : C18H19ClN2O2, FW = 330.80, monoclinic, space group P21/c, a = 12.0348 (13) Å, b = 18.050 (2) Å, c = 7.9752 (9) Å, β = 102.269 (5)˚, V = 1692.9 (3) ų, Z = 4, T = 296 (2) K, d calcd = 1.298 g cm-³, F(000) = 696. Diffraction data were measured with MoKα (λ = 0.71073 Å) radiation at 296 K using a Bruker Kappa Apex 2 CCD system. A total of 2404 unique reflections were measured (θmax = 25.00˚). Data analyses were carried out with the Fast Fourier Transform program. The structures were solved by direct methods using the SHELXS-97¹4 program. Refinements were carried out with a full matrix least squares method against F2 using SHELXL-97.¹5 Non-hydrogen atoms were refined with anisotropic thermal parameters. The final R value was R1 = 0.0375 and wR2 = 0.1202 with I > 2σ(I). Crystallographic data have been deposited at the Cambridge Crystallographic Data Centre with reference number CCDC 773605.