Intramolecular cycloadditions with isobenzofurans XI1 - Synthesis of annulated indoles

Heterocyclic Communications

Volumn 2, Issue 3, 1996, Pages 203-212

  Peters, Olaf ^a   Friedrichsen, Willy ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011213989     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1996.2.3.203     Document Type: Article

References (80)

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20. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
21. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
22. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
23. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
24. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
25. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
26. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
27. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
28. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
29. Previous work in this field: 8a. M.G.Saulnier, G.W.Gribble, Tetrahedron Lett. 1983, 24, 5435. - 8b. C.May, C.J.Moody, J.Chem.Soc., Chem.Commun. 1984, 926. - 8c. G.W.Gribble, M.G.Saulnier, J.Chem.Soc., Chem.Commun. 1984,168, - 8d. G.W.Gribble, G.Saulnier, M.P.Sibi, J.A.Obaza-Nutaitis, J.Org.Chem. 1984, 49, 4518. - 8e. D.A.Davis, G.W.Gribble, Tetrahedron Lett. 1990, 31, 1081. - 8f. G.W.Gribble, Synlett 1991, 289. - 8g. C.J.Moody, K.F.Rahimtola, J.Org.Chem. 1992, 57, 2105. - 8h. U.Pindur, M.Haber, H.Erfanian-Abdoust, Heterocycles 1992, 34, 781. - 8i. Y.Miki, H.Hachiken, Synlett 1993, 933. - 8j. J.Nagel, W.Friedrichsen, T.Debaerdemaeker, Z.Naturforsch. 1993, 486, 213.
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47. 9b, mp 100 °C (100-101 °C)9b).
48. 2H), 7.17-7.43 (m, 3H, Ar-H), 7.93-8.17 (m, 1H, Ar-H), 9.3-10.2 (br s, 1H, COOH).
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51. 3).
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53. 2R, C-1').
54. 3), 168.99 (s, C-11).
55. 3), 164.84 (s, C-11).
56. 4: Cale. 299.1158 Found 287.1157 (MS).
57. 2), 7.17-7.67 (m, 8H, Ar-H), 8,23-8.43 (m, 1H, Ar-H).
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76. 40,41 and will not be repeated here,
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