Benzoannulation of quinones by a cycloaddition-fragmentation approach. A simple synthesis of methoxycarbonyl-substituted polyacenoquinones

Journal of the Chinese Chemical Society

Volumn 51, Issue 1, 2004, Pages 167-174

  Chou, Teh Chang ^a   Hsu, Chia Jung ^a   Chen, Jao Yu ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

Benzoannulation; Diels Alder reactions; Grob fragmentation; Polyacenoquinones

Indexed keywords

1,2,3,4 TETRACHLORO 1,4,4A,12A TETRAHYDRO 1,4 DIMETHOXYMETHANONAPHTHACENE 5,12 DIONE; 1,2,3,4 TETRACHLORO 4,5 DIMETHOXYCYCLOPENTADIENE; 1,4 ANTHRAQUINONE; 1,4 BENZOQUINONE; 1,4 NAPHTHOQUINONE; 1,4 NAPHTHOQUINONE DERIVATIVE; 2,3 DICYANO 1,4 BENZOQUINONE; 2,3 DICYANO 5,6,7,8 TETRACHLORO 4A,5,8,8A TETRAHYDRO 5,8 DIMETHOXYMETHANO 1,4 NAPHTHOQUINONE; 2,3 DICYANO 5,6,7,8 TETRACHLORO 5,8 DIHYDRONAPHTHALENE 1,4 DIOL; 2,3,4 TRICHLORO 5,12 DIOXO 5,12 DIHYDRONAPHTHACENE 1 CARBOXYLIC ACID METHYL ESTER; 2,3,4 TRICHLORO 5,8 DIOXO 5,8 DIHYDRONAPHTHALENE 1 CARBOXYLIC ACID METHYL ESTER; 2,3,4 TRICHLORO 6,7 DICYANO 5,8 DIOXO 5,8 DIHYDRONAPHTHALENE 1 CARBOXYLIC ACID METHYL ESTER; 2,3,4 TRICHLORO 9,10 DIOXO 9,10 DIHYDROANTHRACENE 1 CARBOXYLIC ACID METHYL ESTER; 2,3,4,5,6,7 HEXACHLORO 9,10 DIOXO 9,10 DIHYDROANTHRACENE 1,8 DICARBOXYLIC ACID DIMETHYL ESTER; 2,3,4,5,6,7,8 HEPTACHLORO 9,10 DIOXO 5,8,8A,9,10,10A HEXAHYDRO 5,8 DIMETHOXYMETHANOANTHRACENE 1 CARBOXYLIC ACID METHYL ESTER; 2,3,4,6,7,8 HEXACHLORO 9,10 DIOXO 9,10 DIHYDROANTHRACENE 1,5 DICARBOXYLIC ACID DIMETHYL ESTER; ANTHRAQUINONE DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBONYL DERIVATIVE; DICHLOROMETHANE; ESTER DERIVATIVE; HYDROQUINONE; QUINONE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; BENZOANNULATION; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; FRAGMENTATION REACTION; ISOMER; OXIDATION; ROOM TEMPERATURE;

EID: 2142820098     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200400025     Document Type: Article

References (47)

1. (a) Newcomer, J. S.; McBee, E. T. J. Am. Chem. Soc. 1949, 71, 946.
2. (b) McBee, E. T.; Crain, D. L.; Crain, R. D.; Belohlav, L. R.; Braendlin, H. P. J. Am. Chem. Soc. 1962, 84, 3557.
3. (a) Ungnade, H. E.; McBee, E. T. Chem. Rev. 1958, 58, 249.
4. (b) McBee, E. T.; Diveley, W. R.; Burch, J. E. J. Am. Chem. Soc. 1955, 77, 385.
5. (c) Yates, P.; Eaton, P. E. Tetrahedron 1961, 12, 13.
6. (d) Mackenzie, K. Tetrahedron Lett. 1974, 1023.
7. (e) Jung, M. E.; Kaas, S. M. Tetrahedron Lett. 1989, 30, 641.
8. (f) For a recent review: Khan, F. A.; Prabhudas, B.; Dash, J. J. Prakt. Chem. 2000, 342, 512.
9. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
10. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
11. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
12. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
13. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
14. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
15. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
16. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
17. For examples: (a) Eaton, P. E.; Or, Y. S.; Branca, S. J. Tetrahedron 1986, 42, 1621. (b) Fessner, W. D.; Sedelmeimer, G.; Spurr, P. R.; Rihs, G.; Prinzbach, H. J. Am. Chem. Soc. 1987, 109, 4626. (c) Chou, T.-C.; Chuang, K.-S.; Lin, C.-T. J. Org. Chem. 1988, 53, 5168. (d) Mehta, G.; Padma, S. J. Org. Chem. 1991, 56, 1298. (e) Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501. (f) Chou, T.-C.; Yeh, Y.-L.; Lin, G.-H. Tetrahedron Lett. 1996, 37, 8779. (g) Chou, T.-C.; Lin, G.-H.; Yeh, Y.-L.; Lin, K.-C. J. Chin. Chem. Soc. 1997, 44, 477. (h) Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424. (i) Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783.
18. For examples: (a) Mehta, G.; Mohal, N. Tetrahedron Lett. 1998, 39, 3281. (b) Mehta, G.; Reddy, D. S. Tetrahedron Lett. 1999, 40, 9137. (c) Mehta, G.; Reddy, D. S.; Ramesh, S. S.; Tatu, U. Tetrahedron Lett. 1999, 40, 9141. (d) Mehta, G.; Reddy, D. S. J. Chem. Soc. Perkin Trans. 1 2000, 1399.
19. For examples: (a) Mehta, G.; Mohal, N. Tetrahedron Lett. 1998, 39, 3281. (b) Mehta, G.; Reddy, D. S. Tetrahedron Lett. 1999, 40, 9137. (c) Mehta, G.; Reddy, D. S.; Ramesh, S. S.; Tatu, U. Tetrahedron Lett. 1999, 40, 9141. (d) Mehta, G.; Reddy, D. S. J. Chem. Soc. Perkin Trans. 1 2000, 1399.
20. For examples: (a) Mehta, G.; Mohal, N. Tetrahedron Lett. 1998, 39, 3281. (b) Mehta, G.; Reddy, D. S. Tetrahedron Lett. 1999, 40, 9137. (c) Mehta, G.; Reddy, D. S.; Ramesh, S. S.; Tatu, U. Tetrahedron Lett. 1999, 40, 9141. (d) Mehta, G.; Reddy, D. S. J. Chem. Soc. Perkin Trans. 1 2000, 1399.
21. For examples: (a) Mehta, G.; Mohal, N. Tetrahedron Lett. 1998, 39, 3281. (b) Mehta, G.; Reddy, D. S. Tetrahedron Lett. 1999, 40, 9137. (c) Mehta, G.; Reddy, D. S.; Ramesh, S. S.; Tatu, U. Tetrahedron Lett. 1999, 40, 9141. (d) Mehta, G.; Reddy, D. S. J. Chem. Soc. Perkin Trans. 1 2000, 1399.
22. (a) Grob, C. A.; Baumann, W. Helv. Chim. Acta 1955, 38, 594.
23. (b) Wharton, P. S.; Hiegel, G. A. J. Org. Chem. 1965, 30, 3254.
24. (c) Grob, C. A.; Schiess, P. W. Angew. Chem., Int. Ed. Engl. 1967, 6, 1.
25. (d) Grob, C. A. Angew. Chem., Int. Ed. Engl. 1969, 8, 535.
26. (e) Caine, D. Org. Prep. Proced. Int. 1988, 20, 1.
27. (a) Hoch, P. E. J. Org. Chem. 1961, 26, 2066.
28. (b) Kagi, R. I.; Johnson, B. L. Aust. J. Chem. 1975, 28, 2189.
29. Mitchell, R. H.; Chaudhary, M.; Kamada, T.; Slowey, P. D.; Williams, R. V. Tetrahedron 1986, 42, 1741.
30. (a) Dickmann, J. J. Org. Chem. 1963, 25, 2880.
31. (b) Mackenzie, K. J. Chem. Soc. 1964, 5710.
32. (c) Lustgarten, R. K.; Richey, H. G. J. Am. Chem. Soc. 1974, 96, 6393.
33. (d) Sunko, D. E.; Lovrić, Z.; Vanćik, H. J. Chem. Soc. Chem. Commun. 1985, 1598.
34. (a) Kniel, P. Helv. Chim. Acta 1963, 52, 492.
35. (b) Kniel, P. Helv. Chim. Acta 1965, 91, 837. See also: O'Connor, U.; Rosen, W. J. Org. Chem. 1980, 45, 1824.
36. (b) Kniel, P. Helv. Chim. Acta 1965, 91, 837. See also: O'Connor, U.; Rosen, W. J. Org. Chem. 1980, 45, 1824.
37. (a) Mehta, G.; Padma, S.; Venkatesan, K.; Begum, N. S.; Moorthy, J. N. Indian J. Chem. 1992, 31B, 473.
38. (b) Marchand, A. P.; Alihodzic, S.; Shukla, R. Synth. Commun. 1998, 28, 541.
39. (a) Marchand, A. P.; Chou, T.-C. J. Chem. Soc. Perkin Trans. 1, 1973, 1948.
40. (b) Chou, T.-C.; Chiou, J.-H. J. Chin. Chem. Soc. 1986, 33, 27.
41. (c) Chou, T.-C.; Hong, R-C.; Wu, Y.-F.; Chang, W.-Y; Lin, C.-T.; Lin, K.-J. Tetrahedron 1996, 52, 6325.
42. We also noticed the high sensitivity of cycloadduct 5A toward laboratory illumination and took precaution by wrapping the reaction flask with aluminum foil to minimize contact with light during preparation.
43. Comparable results were found for the reactions in which silica gel was replaced by aluminum oxide.
44. (a) Bedworth, P. V.; Perry, J. W.; Marder, S. R. J. Chem. Soc. Chem. Commun. 1997, 1353.
45. (b) Patney, H. K. Synthesis 1986, 326.
46. (a) Adams, R.; Whitehill, L. N. J. Am. Chem. Soc. 1941, 63, 2073.
47. (b) Perrier, S.; Kochi, J. K. J. Chem. Soc. Perkin Trans 2 1993, 825.