Abnormal Pummerer cyclizations on the indole ring

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5217-5220

  Amat, Mercedes ^a   Bennasar, M Lluïsa ^a   Hadida, Sabine ^a   Sufi, Bilal A ^a   Zulaica, Ester ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE; SULFIDE; SULFONIUM DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION;

EID: 0030586113     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01030-1     Document Type: Article

References (19)

1. 1. (a) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157-405
2. (b) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, Chapter 4.7.
3. (c) Kennedy, M.; McKervey, M. A. Ibid, Vol 7, Chapter 2.4.
4. 2. (a) Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750-4757.
5. (b) Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299-6312.
6. 3. Harris, T. D.; Boekelheide, V. J. Org. Chem. 1976, 41, 2770-2772.
7. 4. Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242-2248.
8. 5. Bennasar, M.-L.; Zulaica, E.; Sufi, B. A.; Bosch, J. Tetrahedron, in press.
9. 3S 464.2133, found 464.2149.
10. 7. Pentacycle 3 was only isolated, although in very low yield (6%), when the Pummerer reaction was effected with trimethylsilyl triflate in the presence of diisopropylethylamine: see reference 5.
11. 8. Bennasar, M.-L.; Zulaica, E.; Jiménez, J.-M.; Bosch, J. J. Org. Chem. 1993, 59, 7756-7767.
12. 9. Amat, M.; Hadida, S.; Sathyanarayana, S.; Bosch, J. Tetrahedron Lett. 1996, 37, 3071-3074.
13. 3O), 54.0 (C-6), 56.7 (CH), 63.4 (C-13b), 81.8 (C-8a), 114.4 (C-12), 116.5 (C-9), 123.1 (C-10), 124.3 (C-11), 127.4 (C-o), 128.7 (C-ipso), 129.6 (C-8b), 130.8 (C-m), 132.1 (C-p), 133.7 (C-12a), 136.8 (C-13a), 168.8 (CO).
14. +, 27), 451 (36), 342 (39), 341 (100), 238 (18), 200 (21).
15. 12. Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490-5492.
16. 13. There are very few examples of Pummerer reactions from β-amino sulfoxides: (a) Takano, S.; Iida, H.; Inomata, K.; Ogasawara, K. Heterocycles 1993, 35, 47-52.
17. (b) Catena, J. L.; Valls, N.; Bosch, J.; Bonjoch; J.; Tetrahedron Lett. 1994, 35, 4433-4436.
18. (c) Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792-5796.
19. 14. To our knowledge, the Pummerer reaction leading to 5b constitutes the first example of a synthetically useful Pummerer cyclization on the indole 3-position in 3-unsubstituted indoles: Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118-1124. See also reference 1.