Synthesis of pyrrolo[1,2-a]quinoxaline and its 4-(1-hydroxyalkyl) derivatives by Lewis acid-catalyzed reactions of 1-(2-isocyanophenyl)pyrrole

Chemistry Letters

Volumn , Issue 6, 1998, Pages 551-552

  Kobayashi, Kazuhiro ^a   Matoba, Takeshi ^a   Irisawa, Susumu ^a   Matsumoto, Takashi ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032381605     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.551     Document Type: Article

References (28)

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18. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
19. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
20. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
21. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
22. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
23. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
24. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
25. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
26. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
27. For recent reports on the synthesis utilizing the carbon-carbon bond formation between isonitrile-carbon and carbonyl-carbon, see: D. Seebach, G. Adam, T. Gees, M. Schiess, and W. Weigand, Chem. Ber., 121, 507 (1988); Y. Hashida, A. Imai, and S. Sekiguchi, J. Heterocycl. Chem., 26, 901 (1989); H. Kunz, W. Pfrengle, and W. Sager, Tetrahedron Lett., 30, 4109 (1989); T. Carofiglio, C. Floriani, A. Chiesi-Villa, and C. Rizzoli, Organometallics, 10, 1659 (1991); M. Murakami, T. Kawano, H. Ito, and Y. Ito, J. Org. Chem., 58, 1458 (1993); R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino, Synthesis, 1994, 672; Y. Makioka, M. Tsuno, K. Takaki, Y. Taniguchi, and Y. Fujiwara, Chem. Lett., 1995, 82; J. P. G. Versleijen, P. M. Faber, H. H. Bodewes, A. H. Braker, D. van Leusen, and A. M. van Leusen, Tetrahedron Lett., 36, 2109 (1995); A. Demharter, W. Hoerl, E. Herdtweck, and I. Ugi, Angew. Chem., Int. Ed. Engl., 35, 173 (1996); A. Keating and R. W. Armstrong, J. Am. Chem. Soc., 118, 2574 (1996); I. Ugi, A. Demharter, W. Hoerl, and T. Schmid, Tetrahedron, 52, 11657 (1996).
28. +, 35%], 195 (100).