A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions

Synlett

Volumn , Issue 9, 1999, Pages 1432-1434

  Arcadi, Antonio ^a   Cacchi, Sandro ^b   Fabrizi, Giancarlo ^b   Marinelli, Fabio ^a   Moro, Leonardo ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

Benzo b furans; Catalysis; Iodocyclization; O alkynylphenols; Palladium

Indexed keywords

BENZOFURAN DERIVATIVE; IODINE; PALLADIUM; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032823767     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2839     Document Type: Article

References (47)

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17. Fürstner, A.; Jumbam, D.N. Tetrahedron 1992, 48, 5991; Hellwinkel, D.; Göke, K. Synthesis 1995, 1135; Ito, Y.; Aoyama, T.; Shioiri, T. Synlett 1997, 1163; Hennings, D.D.; Iwasa, S.; Rawal, V.H. Tetrahedron Lett. 1997, 38, 6379; Du, X.; Armstrong R. W. J. Org. Chem. 1997, 62, 5678; Fuganti, C.; Serra, S. Tetrahedron Lett. 1998, 39, 5609.
18. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
19. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
20. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
21. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
22. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
23. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
24. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
25. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
26. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
27. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
28. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
29. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. I 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
30. Haglund, O.; Nilson, M. Synlett 1991, 723; Dyker, G. J. Org. Chem. 1993, 58, 6426; Kozikowski, A.P.; Ma, D.; Du, L.; Candiani, I.; DeBernardinis, S.; Cabri, W.; Marchi, M.; Bedeschi, A.; Penco, S. Synlett 1993, 269; Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 41, 11803; Bates, R.W.; Rama-Devi, T. Synlett 1995, 1151; Lewin, N.E.; Blumberg, P.M. J. Am. Chem. Soc. 1995, 117, 6666; Larock, R.C.; Yum, E.K.; Doty, M.J.; Sham, K.K.C. J. Org. Chem. 1995, 60, 3270; Amatore, C.; Blart, E.; Genêt, J.P.; Jutand, A.; Lemaire-Audoire, S.; Savignac, M. J. Org. Chem. 1995, 60, 6829; Botta, M.; Summa, V.; Corelli, F.; Di Pietro, G.; Lombardi, P. Tetrahedron Asymmetry 1996, 7, 1263; Fancelli, D.; Fagnola, M.C.; Severino, D.; Bedeschi, A. Tetrahedron Lett. 1997, 38, 2311; Bishop, B.C.; Cottrell, I.F.; Hands, D. Synthesis 1997, 1315; Kundu, N.G.; Pal, M., Mahanty, J.S.; De, M. J. Chem. Soc. Perkin Trans. 1 1997, 19, 2815; Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111.
31. Arcadi, A.; Cacchi, S.; Marinelli, F. Synthesis 1986, 749.
32. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
33. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
34. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
35. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
36. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
37. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
38. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
39. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
40. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
41. Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280; Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741; Cacchi, S.; Fabrizi, G.; Moro, L. Terahedron Lett. 1998, 39, 5101. Bew, S.; Knigth, D.W. J. Chem. Soc., Chem. Commun. 1996, 1007; Kitagawa, O.; Fujita, M.; Li, H.; Taguchi, T. Tetrahedron Lett. 1997, 38, 615; Stefani, H.A.; Petragnani, N.; Valduga, C.J.; Brandt, C.A. Tetrahedron Lett. 1997, 38, 4977; Lavilla, R.; Coll, M.; Nicolàs, M.; Bosch, J. Tetrahedron Lett. 1998, 39, 5089; Ren, X.-F.; Konaklieva, M.I.; Shi, H.; Dickey, S.; Lim, D.V.; Gonzales, J.; Turos, E. J. Org. Chem. 1998, 63, 8898; Ma, S.; Shi, Z.; Yu, Z. Tetrahedron Lett. 1999, 40, 2393. A similar reaction producing 2-phenyl-3-iodobenzo[b]furan from o-(phenylethynyl)phenol, n-butyl lithium, and iodine has been described: Buckle, D.R.; Rockell, C.J.M. J. Chem. Soc. Perkin Trans 1 1985, 2443.
42. 4), and concentrated under vacuum.
43. +, 100), 193 (19), 165 (59). Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363. Mopac 6.0 residual charge data for acetylenic carbon atoms of 1a, c, f, and g using the Hamiltonian AM 1 of substructures with optimized bond lengths, bond angles, and torsional angles, are as follows: equation presented
44. 3) δ 166.5, 152.4, 151.0, 138.4, 134.4, 133.5, 132.6, 131.4, 130.9, 130.5, 130.1, 129.1, 128.8, 128.5, 126.9, 126.2, 119.6, 116.4, 110.7, 61.1, 21.4, 14.4.
45. Benaglia, M.; Toyota, S.; Woods, C.R.; Siegel, J.S. Tetrahedron Lett. 1997, 38, 4737; Yamamura, K.; Yamane, T.; Tagaki, H.; Miyake, H.; Heterocycles 1997, 45, 467.
46. Benaglia, M.; Toyota, S.; Woods, C.R.; Siegel, J.S. Tetrahedron Lett. 1997, 38, 4737; Yamamura, K.; Yamane, T.; Tagaki, H.; Miyake, H.; Heterocycles 1997, 45, 467.
47. Larock, R.C.; Harrison, L.W. J. Am. Chem. Soc. 1984, 106, 4218.