Synthesis of isocoumarins and α-pyrones via electrophilic cyclization

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 5936-5942

  Yao, Tuanli ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION CONDITIONS;

POLYCYCLIC AROMATIC HYDROCARBONS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ESTERS;

2 PYRONE DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BENZOIC ACID DERIVATIVE; ISOCOUMARIN DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0038373080     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034308v     Document Type: Article

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26. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
27. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
28. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
29. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
30. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
31. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
32. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
33. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
34. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
35. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
36. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
37. 2 into dialkyl-substituted alkyne dimers: (b) Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1980, 53, 3329. Photoisomerization of 4-pyrones: (c) West, F. G.; Hartke-Karger, C.; Koch, D. J.; Kuehn, C. E.; Arif, A. M. J. Org. Chem. 1993, 58, 6795. (d) Pavlik, J. W.; Patten, A. D.; Bolin, D. R.; Bradford, K. C.; Clennan, E. L. J. Org. Chem. 1984, 49, 4523. (e) Ishibe, N.; Yutaka, S. J. Org. Chem, 1978, 43, 2138. (f) Ishibe, N.; Sunami, M.; Odani, M. J. Am. Chem. Soc. 1973, 95, 463. Oxidation of dienones: (g) Takata, T.; Tajima, R.; Ando, W. Chem. Lett. 1985, 665. (h) Ho, T. L.; Hall, T. W.; Wong, C. M. Synth. Commun. 1973, 3, 79. Reaction of sulfonium ylides with diphenylcyclopropenone: (i) Hayasi, Y.; Nozaki, H. Tetrahedron 1971, 27, 3085. (j) Kotrestou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161. (k) Tsuda, T.; Morikawa, S.; Saegusa, T. J. Chem. Soc., Chem. Commun. 1989, 9. (l) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461. (m) Cerezo, S.; Moreno-Mañas, M.; Pleixats, R. Tetrahedron Lett. 1998, 54, 7813. (n) Fringuelli, F.; Piermatt, O.; Pizzo, F. Heterocycles 1999, 50, 611. (o) Tominaga, Y. Yuki Gosei Kagaku Kyokaishi 1989, 47, 413.
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