Synlett 2009(15): 2542-2544  
DOI: 10.1055/s-0029-1217736
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient and Direct Solvent-Free Synthesis of Naphtho[1,2-b]furans, Naphtho[2,1-b]furans, and Furo[3,2-c]chromenes

Mehdi Adib*a, Mohammad Mahdavia, Sharareh Bagherzadeha, Hamid Reza Bijanzadehb
a School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
Fax: +98(21)66495291; e-Mail: madib@khayam.ut.ac.ir;
b Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran
Further Information

Publication History

Received 9 February 2009
Publication Date:
27 August 2009 (online)

Abstract

An efficient and direct synthesis of naphtho[1,2-b]furans, naphtho[2,1-b]furans, and furo[3,2-c]chromenes is described. Heating a mixture of a naphthol or 4-hydroxycoumarin, an isocyanide, and an aldehyde under an argon atmosphere and solvent-free conditions afforded the title compounds in excellent yields.

    References and Notes

  • 1 Abdul-Aziz M. Auping JV. Meador MA. J. Org. Chem.  1995,  60:  1303 
  • 2 Frederiksen PK. Jorgensen M. Ogilby PR. J. Am. Chem. Soc.  2001,  123:  1215 
  • 3 Sheats JR. Anthoniadis H. Hueschen M. Leonard W. Miller J. Moon R. Roitman D. Stocking A. Science  1996,  273:  884 
  • 4 Hide F. Díaz-Garzía MA. Schwartz BJ. Heeger AJ. Acc. Chem. Res.  1997,  30:  430 
  • 5 Albota M. Beljonne D. Brédas J.-L. Ehrlich JE. Fu J.-Y. Heikal AA. Hess SE. Kogej T. Levin MD. Marder SR. McCord-Maughon D. Perry JW. Rökel H. Rumi M. Subramaniam G. Webb WW. Wu X.-L. Xu C. Science  1998,  281:  1653 
  • 6a Bohlmann F. Zdero C. Chem. Ber.  1977,  110:  487 
  • 6b Braga de Oliveira A. De Oliveira GG. Carazza F. Braz Filho R. Moreira Bacha CT. Bauer L. Silva GAde AB. Siqueira NCS. Tetrahedron Lett.  1978,  30:  2653 
  • 7 Qian X. Zhang Y. Ni C. Hua. Lig. Dax. Xue.  1994,  20:  336 ; Chem. Abstr. 1994,  121:  3718t 
  • 8 Einhorn J. Demerseman P. Royer R. Cavier R. Gayral P. Eur. J. Med. Chem.  1984,  405 
  • 9 Giovanninetti G. Cavrini V. Chiarini A. Garuti L. Mannini-Palenzona A. Farmaco, Ed. Sci.  1974,  29:  375 
  • 10 Gaggi R. Giovanninetti G. Garuti L. Farmaco, Ed. Sci.  1982,  37:  149 
  • 11a Hranjec M. Grdisa M. Pavelic K. Boykin DW. Karminski-Zamola G. Farmaco  2003,  58:  1319 
  • 11b Mahadevan KM. Padmashali B. Vaidya VP. Indian J. Heterocycl. Chem.  2001,  11:  15 
  • 11c Mahadevan KM. Vaidya VP. Indian J. Pharm. Sci.  2003,  65:  128 
  • 12a Ronto G. Grof P. Buisson JP. Einhorn J. Demerseman P. Mutagenesis  1992,  7:  243 
  • 12b Debnath AK. Hansch C. Kim KH. Martin YC. J. Med. Chem.  1993,  36:  1007 
  • 13 Nair V. Menon RS. Vinod AU. Viji S. Tetrahedron Lett.  2002,  43:  2293 
  • 14 El Kaïm L. Grimaud L. Oble J. Org. Biomol. Chem.  2006,  4:  3410 
  • 15a Solvent-Free Organic Synthesis   Tanaka K. Wiley-VCH; Weinheim: 2004. 
  • 15b Tanaka K. Toda F. Chem. Rev.  2000,  100:  1025 
  • 16a Adib M. Sayahi MH. Ziyadi H. Zhu LG. Bijanzadeh HR. Synthesis  2008,  3289 
  • 16b Adib M. Sheibani E. Zhu LG. Bijanzadeh HR. Synlett  2008,  2941 
  • 16c Adib M. Mohammadi B. Bijanzadeh HR. Synlett  2008,  3180 
  • 16d Adib M. Mohammadi B. Bijanzadeh HR. Synlett  2008,  177 
  • 16e Adib M. Sayahi MH. Ziyadi H. Bijanzadeh HR. Zhu LG. Tetrahedron  2007,  63:  11135 
  • 16f Adib M. Aali Koloogani S. Abbasi A. Bijanzadeh HR. Synthesis  2007,  3056 
  • 16g Adib M. Sheibani E. Abbasi A. Bijanzadeh HR. Tetrahedron Lett.  2007,  48:  1179 
  • 16h Adib M. Sheibani E. Mostofi M. Ghanbary K. Bijanzadeh HR. Tetrahedron  2006,  62:  3435 
  • 16i Adib M. Mahdavi M. Mahmoodi N. Pirelahi H. Bijanzadeh HR. Synlett  2006,  1765 
17

Typical Procedure: Preparation of N - tert -Butyl-3-phenylnaphtho[1,2- b ]furan-2-amine (7b)
A mixture of α-naphthol (0.288 g, 2 mmol), tert-butyl isocyanide (0.166 g, 2 mmol), and benzaldehyde (0.212 g, 2 mmol) was stirred at 180 ˚C in a sealed glass vial under an argon atmosphere for 1.5 h. Then the reaction mixture was cooled to r.t., and the residue was purified by column chromatography using 4:1 n-hexane-EtOAc as eluent.
The solvent was removed under argon atmosphere, and the product was obtained as colorless crystals. Yield 0.58 g (93%); mp 145 ˚C. ¹H NMR (500.1 MHz, CDCl3): δ = 1.62 [s, 9 H, C(CH3)3], 4.49 (br s, 1 H, NH), 7.47 (t, J = 7.1 Hz, 1 H, CH), 7.54 (t, J = 7.1 Hz, 1 H, CH), 7.65 (dd, J = 7.7, 7.8 Hz, 2 H, 2 × CH), 7.71 (t, J = 7.9 Hz, 1 H, CH), 7.77 (dd, J = 0.9, 7.9 Hz, 2 H, 2 × CH), 7.79 (d, J = 8.6 Hz, 1 H, CH), 7.83 (d, J = 8.5 Hz, 1 H, CH), 8.04 (d, J = 8.2 Hz, 1 H, CH), 8.42 (d, J = 8.2 Hz, 1 H, CH). ¹³C NMR (125.8 MHz, CDCl3): δ = 30.71 [C(CH3)3], 53.81 [C(CH3)3], 100.58 (ONC=C), 117.68, 119.33 (2 × CH), 121.06 (C), 123.37 and 123.66 (2 × CH), 125.03 (C), 126.29, 126.35, 128.21, 128.62, 129.36 (5 × CH), 130.17, 133.89, 144.96, 154.67 (4 × C). Anal. Calcd for C22H21NO (315.41): C, 83.78; H, 6.71; N, 4.44. Found: C, 83.7; H, 6.8; N, 4.2.
2-( tert -Butylamino)-3-(4-methylphenyl)-4 H -furo[3,2- c ]chromen-4-one (7o)
Yield 0.66 g (95%); yellow crystals; mp 140-141 ˚C. ¹H NMR (500.1 MHz, CDCl3): δ = 1.39 [s, 9 H, C(CH3)3], 2.40 (s, 3 H, CH3), 4.20 (br s, 1 H, NH), 7.27 (d, J = 7.9 Hz, 2 H, 2 × CH), 7.28-7.30 (m, 1 H, CH), 7.38-7.41 (m, 2 H, 2 × CH), 7.43 (d, J = 7.9 Hz, 2 H, 2 × CH), 7.77 (d, J = 7.8 Hz, 1 H, CH). ¹³C NMR (125.8 MHz, CDCl3): δ = 21.28 (CH3), 30.44 [C(CH3)3], 53.98 [C(CH3)3], 103.28 (ONC=C), 110.39, 112.88 (2 × C), 116.89, 119.71, 124.19 (3 × CH), 127.59 (C), 128.93, 129.26, 129.34 (3 × CH), 136.80, 150.77, 151.56, 154.81, 157.76 (5 × C). Anal. Calcd for C22H21NO3 (347.41): C, 76.06; H, 6.09; N, 4.03. Found: C, 76.1; H, 6.1; N, 4.0.