A three-component reaction of phenol, aldehyde, and active methylene substrate under Lewis acid catalysis: Successful trapping of o-quinone methide to afford benzopyran systems

Chemistry Letters

Volumn 33, Issue 8, 2004, Pages 1058-1059

  Mashraqui, Sabir H ^a   Paul, Mamta B ^a   Mistry, Hitesh D ^a   Ghadigaonkar, Shailesh ^a   Meetsma, Auke ^b  

^a UNIVERSITY OF MUMBAI   (India)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZOPYRAN DERIVATIVE; CARBENE; LEWIS ACID; PHENOL; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 8844222050     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.1058     Document Type: Article

References (34)

1. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
2. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
3. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
4. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
5. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
6. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
7. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
8. For leading reviews on MCR, see: a) B. M. Trost, Angew. Chem., Int. Ed. Engl., 34, 259 (1995). b) P. Eilbracht and A. Schimdt, Chem. Rev., 99, 3329 (1999). c) L. F. Tietze, Chem. Rev., 96, 137 (1996). d) P. J. Parsons, C. S. Penkett and A. J. Shell, Chem. Rev., 96, 195 (1996). e) T. L. Ho, "Tandem Reactions," John Wiley & Sons, New York (1992). f) A. Domling and I. Ugi, Angew. Chem., Int. Ed. Engl., 32, 563 (1993). g) R. A. Bunce, Tetrahedron, 48, 13103 (1995). h) I. Ugi, Pure Appl. Chem., 77, 187 (2001).
9. R. W. Van De Water and T. R. R. Pettus, Tetrahedron, 58, 5367 (2002).
10. a) G. Desimoni and G. Tacconi, Chem. Rev., 75, 651 (1975).
11. b) P. Wan, B. Backer, L. Diao, M. Fischer, Y. Shi, and C. Yang, Can. J. Chem., 74, 465 (1996).
12. c) D. L. Boger and S. Weinreb, Hetero Diles-Alder Meth., 1987, 193.
13. a) A. B. Turner, Q. Rev., 18, 347 (1964).
14. b) W. R. Schleigh, Org. Chem. Bull., 43, 1 (1971).
15. a) P. D. Gardner, J. Am. Chem. Soc., 51, 3364 (1959).
16. b) A. Merijan and P. D. Gardner, J. Org. Chem., 30, 3965 (1965).
17. c) S. R. Angle, J. D. Rainer, and Woytowiez, J. Org. Chem., 62, 5884 (1997).
18. d) E. Fanghanel, J. Bockelmann, N. Grossman, and D. Pfeifer, J. Prakt. Chem., 328, 724 (1986).
19. a) A. Wolff, V. Boehmer, W. Vogt, F. Ugozzoli, and G. D. Andreetti, J. Org. Chem., 55, 5665 (1990).
20. b) K. W. No, J. E. Kim, and K. M. Kwon, Tetrahedron Lett., 36, 844453 (1995).
21. c) V. Allan, J. A. Gainnini, D. D. Whitesides, and H. Thomas, J. Org. Chem., 47, 820 (1882).
22. d) O. Sirkecioglue, N. Talini, and A. Akar, J. Chem. Res., Synop., 1995, 502.
23. 3: C, 80.21; H, 5.85%. found: C, 80.36; H, 6.13%.
24. 2O catalysis.
25. According to a referee, regioselective formation of benzopyrans via 2 + 4 addition of o-QM with the enol of active methylene substrates, followed by dehydration is also possible.
26. Elemental analysis and spectral data for products cited in the Table 1 are given in the supplimentary information. In some cases (Entries 1-3), low polar product(s) formed in minor amounts have not been characterised.
27. The X-ray crystallographic data of 18 have been submitted to the Cambridge data-base as a file: CCDC 230653.
28. Pyranyl heterocycles, see a) R. P. Hsung, J. Org. Chem., 62, 7904 (1997). b) L.-L. Wei, R. P. Hsungg, H. Xiong, J. A. Mulder, and N. T. Nkansah, Org. Lett., 1, 2145 (1999). c) R. P. Hsung, Heterocycles, 48, 421 (1998).
29. Pyranyl heterocycles, see a) R. P. Hsung, J. Org. Chem., 62, 7904 (1997). b) L.-L. Wei, R. P. Hsungg, H. Xiong, J. A. Mulder, and N. T. Nkansah, Org. Lett., 1, 2145 (1999). c) R. P. Hsung, Heterocycles, 48, 421 (1998).
30. Pyranyl heterocycles, see a) R. P. Hsung, J. Org. Chem., 62, 7904 (1997). b) L.-L. Wei, R. P. Hsungg, H. Xiong, J. A. Mulder, and N. T. Nkansah, Org. Lett., 1, 2145 (1999). c) R. P. Hsung, Heterocycles, 48, 421 (1998).
31. K. C. Nicolaou, J. A. Pfefferkorn, S. Barluenga, H. J. Mitchell, A. J. Roecker, and G.-Q. Cao, J. Am. Chem. Soc., 122, 9968 (2000).
32. a) A. Ogundaini, M. Farah, and P. Perera, J. Nat. Prod., 59, 587 (1996).
33. b) M. Chino, K. Nishikawa, A. Yamada, M. Ohsono, T. Sawa, F. Hanaoka, M. Ishizuka, and T. Takeuchi, J. Antibiot., 51, 480 (1998).
34. c) C. P. Dell, Curr. Med. Chem., 5, 179 (1998).