SnCl4-catalyzed reaction of o-benzoquinones and aryl acetylenes: An unprecedented one-pot synthesis of tropone derivatives

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7533-7536

  Nair, Vijay ^a   Sethumadhavan, D ^a   Nair, Smitha M ^a   Rath, Nigam P ^b   Eigendorf, Guenter K ^c  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^c UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DECARBONYLATION;

ACETYLENE; CATALYSIS; DERIVATIVES; SYNTHESIS (CHEMICAL);

TIN COMPOUNDS;

ACETYLENE; BENZOQUINONE DERIVATIVE; TIN CHLORIDE; TROPONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLOADDITION; DECARBONYLATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037131252     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo016098x     Document Type: Article

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23. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
24. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
25. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
26. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
27. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
28. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
29. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
30. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
31. Tropones and Tropolones have attracted considerable interest due to their novel structure and presence in a number of natural products. Consequently, a large number of methods have been developed for the synthesis of this ring system. A few selected references are given here. (a) Silverton, J. V.; Kabuto, C.; Buk, K. T.; Cava, M. P. J. Am. Chem. Soc. 1977, 99, 6708. (b) Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6713. (c) Nair, V.; Powell, D. W.; Suri, S. C. Synth. Commun. 1987, 17, 1897. (d) Suri, S. C.; Nair, V. Synthesis 1990, 695. (e) Davies, H. M. L.; Clark, T. J.; Kimmer, G. F. J. Org. Chem. 1991, 56, 6440 and references therein. (f) Banwell, M. G.; Corbett, M.; Mackay, M. F.; Richards, S. L. J. Chem. Soc., Perkin Trans. 1 1992, 1329. (g) Boger, D. L.; Zhu, Y. J. Org. Chem. 1994, 59, 1329. (h) Dygutsch, D. P.; Neumann, W. P.; Peterseim, M. Synlett 1994, 1329. (i) Lee, J. C.; Jin, S.; Cha, J. K. J. Org. Chem. 1998, 63, 2804. (j) Nenajdenko, V. G.; Baraznenok, I. L.; Balenkova, E. S.; J. Org. Chem. 1998, 63, 6132. (k) Lee, J. C.; Cho, S. Y.; Cha, J. K. Tetrahedron Lett. 1999, 40, 7675. (l) Sendelbach, S.; Schwetzler-Raschke, R.; Radl, A.; Kaiser, R.; Henle, G. H.; Korfant, H.; Reiner, S.; Fohlisch, B. J. Org. Chem. 1999, 64, 3398.
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