Erratum: Reaction of 3/2-formylindoles with TOSMIC: Formation of indolyloxazoles and stable indolyl primary enamines (Tetrahedron (2005) 61 (1793) DOI: 10.1016/j.tet.2004.12.022);Reaction of 3/2-formylindoles with TOSMIC: Formation of indolyloxazoles and stable indolyl primary enamines

Tetrahedron

Volumn 61, Issue 7, 2005, Pages 1793-1801

  Chakrabarty, Manas ^a   Basak, Ramkrishna ^a   Harigaya, Yoshihiro ^b   Takayanagi, Hiroaki ^b  

^a BOSE INSTITUTE   (India)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

3 Formylindoles; Base; Indolyl primary enamines; Indolyloxazoles; TOSMIC

Indexed keywords

2 FORMYLSKATOLE; 3 FORMYLINDOLE; CYANIDE; ENAMINE; FORMAMIDE DERIVATIVE; INDOLE DERIVATIVE; METHANOL; N (1 TOSYL 2 SKATOLYL)ETHENYLFORMAMIDE; OXAZOLE DERIVATIVE; POTASSIUM CARBONATE; SKATOLE; TOSYLMETHYLISOCYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIASTEREOISOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 12944298265     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.037     Document Type: Erratum

References (64)

1. K. Schofield, M.R. Grimmett, and B.R.T. Keene The Azoles 1976 Cambridge University Press Cambridge
2. J.A. Joule, and K. Mills Heterocyclic Chemistry 4th ed. 2000 Blackwell Science Oxford, UK Chapter 21
3. L. Zirngibl Azoles. Antifungal Active Substances - Synthesis and Uses 1997 Wiley-VCH London
4. J.A. Roesener, and P.J. Scheuer J. Am. Chem. Soc. 108 1986 846
5. S. Matsunaga, N. Fusetani, and K. Hashimoto J. Am. Chem. Soc. 108 1986 847
6. P.A. Searle, and T.F. Molinski J. Am. Chem. Soc. 117 1995 8126
7. M. Chakrabarty, N. Ghosh, and Y. Harigaya Tetrahedron Lett. 45 2004 4955
8. M. Chakrabarty, S. Sarkar, and Y. Harigaya Synthesis 2003 2292
9. M. Chakrabarty, R. Basak, N. Ghosh, and Y. Harigaya Tetrahedron 60 2004 1941
10. M. Chakrabarty, and S. Sarkar Tetrahedron Lett. 44 2003 8131
11. D.S. Bhate, R.K. Hulyalkar, and S.K. Menon Experientia 16 1960 56
12. B.S. Joshi, W.I. Taylor, D.S. Bhate, and S.S. Karmakar Tetrahedron 19 1963 1437
13. Y. Koyama, K. Yokose, and L.J. Dolby J. Agric. Biol. Chem. 45 1981 1285
14. K. Umehara, K. Yoshida, M. Okamoto, M. Iwami, H. Tanaka, M. Kohsaka, and H. Imanaka J. Antibiot. 37 1984 1153
15. M. Noltenmeyer, and G.M. Sheldrick J. Antibiot. 35 1982 449
16. G.R. Pettit, J.C. Knight, D.L. Herald, R. Davenport, R.K. Pettit, B.E. Tucker, and J.M. Schmidt J. Nat. Prod. 65 2002 1793
17. M.J. Narasimhan Jr., and V.G. Ganla Hindustan Antibiot. Bull. 9 1967 138
18. T. Takeuchi, K. Ogawa, H. Iinuma, H. Suda, K. Ukita, T. Nagatsu, M. Kato, and H. Umezawa J. Antibiot. 26 1973 162
19. M. Somei, H. Sato, N. Komura, and C. Kaneko Heterocycles 23 1985 1101
20. Y. Oikawa, T. Yoshioka, K. Mohri, and O. Yonemitsu Heterocycles 12 1979 1457
21. T. Yoshioka, K. Mohri, Y. Oikawa, and O. Yonemitsu J. Chem. Res. (S) 1981 194
22. K.J. Doyle, and C.J. Moody Synthesis 1994 1021
23. H.A. Houwing, J. Wildeman, and A.M. van Leusen J. Heterocycl. Chem. 18 1981 1133
24. P. Molina, P.M. Fresneda, and P. Almendros Synthesis 1993 54
25. A.M. van Leusen, B.E. Hoogenboom, and H. Siderius Tetrahedron Lett. 1972 2369
26. B.A. Kulkarni, and A. Ganesan Tetrahedron Lett. 40 1999 5637
27. D. van Leusen, and A.M. van Leusen Organic Reactions Vol. 57 2001 Wiley New York 417
28. H. Saikachi, T. Kitagawa, H. Sasaki, and A.M. van Leusen Chem. Pharm. Bull. 27 1979 793
29. H. Saikachi, T. Kitagawa, H. Sasaki, and A.M. van Leusen Chem. Pharm. Bull. 30 1982 4199
30. J.Y. Merour, and A. Buzas Synth. Commun. 18 1988 2331
31. O.H. Oldenziel, D. van Leusen, and A.M. van Leusen J. Org. Chem. 42 1977 3114
32. J.C. Jagt, and A.M. van Leusen J. Org. Chem. 39 1974 564
33. C. Moureau, and G. Mignonac Compt. Rend. 158 1914 1395
34. R.W. Layer Chem. Rev. 63 1963 489
35. C. Cratky Helv. Chim. Acta 61 1978 3108
36. M. Masaki, C. Shin, H. Kurita, and M. Ohta Chem. Commun. 1968 1447
37. C. Shin, M. Masaki, and M. Ohta Bull. Chem. Soc. Jpn. 44 1971 1657
38. H. Ahlbrecht, and G. Papke Tetrahedron Lett. 1972 4443
39. H. Ahlbrecht, and S. Fischer Tetrahedron 29 1973 659
40. H. Ahlbrecht, J. Blecher, H. Hanisch, G. Papke, and M.T. Reiner Tetrahedron 29 1973 3079
41. H. Ahlbrecht, and G. Papke Tetrahedron 30 1974 2571
42. H. Ahlbrecht, W. Funk, and M.T. Reiner Tetrahedron 32 1976 479
43. 2)=0.1810 (all data). Two crystallographically independent molecules exist in an asymmetric unit and are represented by the carbon number C1-C19 and C20-C38. CCDC-244416 contains the supplementary crystallographic data for this paper. These data can be obtained via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).
44. G. Erker, R. Pfaff, C. Krüger, M. Nolte, and R. Goddard Chem. Ber. 125 1992 1669
45. G. Erker, and R. Pfaff Organometallics 12 1993 1921
46. G. Erker, R. Pfaff, D. Kowalski, E.-U. Würthwein, C. Krüger, and R. Goddard J. Org. Chem. 58 1993 6771
47. M.P. Kirkup, and R.E. Moore Tetrahedron Lett. 24 1983 2087
48. K. Azumi, H. Yokosawa, and S. Ishii Biochemistry 29 1990 159
49. E. Dumdei, and R.J. Andersen J. Nat. Prod. 56 1993 792
50. T. Kagamizono, N. Sakai, K. Arai, K. Kobinata, and H. Osada Tetrahedron Lett. 38 1997 1223
51. S.G. Toske, P.R. Jensen, C.A. Kauffman, and W. Fenical Tetrahedron 54 1998 13439
52. J.A. Palermo, P.B. Flower, and A.M. Seldes Tetrahedron Lett. 32 1992 3097
53. D. Davyt, W. Entz, R. Fernandez, R. Mariezcurrena, A.W. Mambru, J. Saldana, L. Dominguez, J. Coll, and E. Manta J. Nat. Prod. 61 1998 1560
54. H.R. Bokesch, L.K. Pannell, T.C. McKee, and M.R. Boyd Tetrahedron Lett. 41 2000 6305
55. U. Schöllkopf, R. Schröder, and E. Blume Liebigs Ann. Chem. 766 1972 130
56. U. Schöllkopf, and R. Schröder Angew. Chem., Int. Ed. Engl. 12 1973 407
57. B.G. Gower, and E. Leete J. Am. Chem. Soc. 85 1963 3683
58. T. Kurihara, T. Fujimoto, S. Harusawa, and R. Yoneda Synthesis 1987 396
59. A. Kalir, and S. Szara J. Med. Chem. 9 1966 793
60. D.D. Evans Aust. J. Chem. 26 1973 2555
61. W.L. Chan, D.D. Ho, C.P. Lau, K.H. Wat, Y.C. Kong, K.F. Cheng, T.T. Wong, and T.Y. Chan Eur. J. Med. Chem. 26 1991 387
62. S. Shin, N. Takahashi, and Y. Yonezawa Chem. Pharm. Bull. 38 1990 2020
63. A. Chatterjee, and K.M. Biswas J. Org. Chem. 38 1973 4002
64. S. Kumar, V. Kumar, and S.S. Chimni Tetrahedron Lett. 43 2002 8029