Reactivity of naphthol towards nucleophiles in anodic oxidation

Tetrahedron

Volumn 58, Issue 37, 2002, Pages 7485-7489

  El Seedi, Hesham R ^a,b   Yamamura, Shosuke ^a   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

^b Menoufia University   (Egypt)

Author keywords

4 methoxy 1 naphthol; Anodic oxidation; Cycloaddition; Electrochemical reaction

Indexed keywords

1 METHOXY 4 PROPENYLBENZENE; 1 NAPHTHOL DERIVATIVE; 2 (1 HYDROXY 4 METHOXY 2 NAPHTHYL) 4 METHOXY 1 NAPHTHOL; 2 (2H BENZO[D] 1,3 DIOXOL 5 YL) 2,3 DIHYDRO 5 METHOXY 3 METHYLNAPHTHOL[1,2 B]FURAN; 2 ETHOXY 5 METHOXY 2,3 DIHYDRONAPHTHO[1,2 B]FURAN; 2 TETRAHYDROFURAN 2 YLNAPHTHALENE 1,4 DIONE; 2,3 DIHYDRO 5 METHOXY 2 (4 METHOXYPHENYL) 3 METHYLNAPHTHO[1,2 B]FURAN; 2,3,3A,10A TETRAHYDRO 5 METHOXYFURO[2,3 B]NAPHTHO[2,1 D]FURAN; 3,4,4A,11A TETRAHYDRO 6 METHOXYNAPHTHO[2',1' 4,5]FURO[2,3 B] 2H PYRAN; 4 METHOXY 1 NAPHTHOL; BENZENE DERIVATIVE; DIMER; ETHER DERIVATIVE; ETHYLVINYL ETHER; FURAN DERIVATIVE; ISOSAFROLE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; ELECTROCHEMISTRY; ELECTROLYSIS; METHODOLOGY; OXIDATION; PRIORITY JOURNAL;

EID: 0037048462     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00829-3     Document Type: Article

References (34)

1. For instance: (a) Sainsbury M. Tetrahedron. 36:1980;3327-3359 (b) Ferraz H.M.C., Silva L.F. Jr., Vieira T.de O. Synthesis. 1999;2001-2023 (c) Sawyer J.S. Tetrahedron. 56:2000;5045-5065 (d) Tohma H. Yakugakuzasshi. 120:2000;620-629 (e) Pelter A., Ward R.S. Tetrahedron. 57:2001;273-282.
2. For instance: (a) Sainsbury M. Tetrahedron. 36:1980;3327-3359 (b) Ferraz H.M.C., Silva L.F. Jr., Vieira T.de O. Synthesis. 1999;2001-2023 (c) Sawyer J.S. Tetrahedron. 56:2000;5045-5065 (d) Tohma H. Yakugakuzasshi. 120:2000;620-629 (e) Pelter A., Ward R.S. Tetrahedron. 57:2001;273-282.
3. For instance: (a) Sainsbury M. Tetrahedron. 36:1980;3327-3359 (b) Ferraz H.M.C., Silva L.F. Jr., Vieira T.de O. Synthesis. 1999;2001-2023 (c) Sawyer J.S. Tetrahedron. 56:2000;5045-5065 (d) Tohma H. Yakugakuzasshi. 120:2000;620-629 (e) Pelter A., Ward R.S. Tetrahedron. 57:2001;273-282.
4. For instance: (a) Sainsbury M. Tetrahedron. 36:1980;3327-3359 (b) Ferraz H.M.C., Silva L.F. Jr., Vieira T.de O. Synthesis. 1999;2001-2023 (c) Sawyer J.S. Tetrahedron. 56:2000;5045-5065 (d) Tohma H. Yakugakuzasshi. 120:2000;620-629 (e) Pelter A., Ward R.S. Tetrahedron. 57:2001;273-282.
5. For instance: (a) Sainsbury M. Tetrahedron. 36:1980;3327-3359 (b) Ferraz H.M.C., Silva L.F. Jr., Vieira T.de O. Synthesis. 1999;2001-2023 (c) Sawyer J.S. Tetrahedron. 56:2000;5045-5065 (d) Tohma H. Yakugakuzasshi. 120:2000;620-629 (e) Pelter A., Ward R.S. Tetrahedron. 57:2001;273-282.
6. Bringmann G., Walter R., Weirich R. Angew. Chem. Int. Ed. Engl. 29:1990;977-991.
7. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
8. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
9. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
10. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
11. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
12. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
13. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
14. For instance: (a) Krohn K., Rieger H., Brüggmann K. Synthesis. 1990;1141-1143 (b) Barret R., Daudon M. Tetrahedron Lett. 31:1990;4871-4872 (c) Matsumoto T., Imai S., Yamamoto N. Bull. Chem. Soc. Jpn. 61:1988;911-919 (d) Bao J., Wulff W.D., Dominy J.B., Fumo M.J., Grant E.B., Rob A.C., Whitcomb M.C., Yeung S.M., Ostrander R.L., Rheingold A.L. J. Am. Chem. Soc. 118:1996;3392-3405 (e) Hwang D.R., Chen C.P., Uang B.J. Chem. Commun. 1999;1207-1208 (f) Doussot J., Guy A., Ferroud C. Tetrahedron Lett. 41:2000;2545-2547 (g) Chu C.Y., Hwang D.-R., Wang S.-K., Uang B.-J. Chem. Commun. 2001;980-981 (h) Tanoue Y., Sakata K., Hashimoto M., Morishita S., Hamada M., Kai N., Nagai T. Tetrahedron. 58:2002;99-104.
15. For instance: (a) El-Mobayed M., Ismail N., Abo El-Enein G., Abd El-Haleem E. J. Chem. Soc. Pak. 8:1986;305-310
16. (b) Kashiwagi Y., Ono H., Osa T. Chem. Lett. 1993;81-84.
17. Yamamura S., Nishiyama S. Synlett. 2002;533-543. Many references cited therein.
18. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
19. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
20. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
21. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
22. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
23. Related anodic oxidations: (a) Shizuri Y., Nakamura K., Yamamura S. J. Chem. Soc. Chem. Commun. 1985;530-531 (b) Gates B.D., Dalidowicz P., Tebben A., Wang S., Swenton J.S. J. Org. Chem. 57:1992;2135-2143 (c) Kerns M.L., Conroy S.M., Swenton J.S. Tetrahedron Lett. 35:1994;7529-7532 (d) Chiba K., Jinno M., Kuramoto R., Tada M. Tetrahedron Lett. 39:1998;5527-5530 (e) Chiba K., Arakawa T., Tada M. J. Chem. Soc., Perkin Trans. 1. 1998;2939-2942 (f) Chiba K., Fukuda M., Kim S., Kitano Y., Tada M. J. Org. Chem. 64:1999;7654-7656.
24. Part of this work was published: El-Seedi H.R., Yamamura S., Nishiyama S. Tetrahedron Lett. 43:2002;3301-3304.
25. (a) Tanoue Y., Terada A., Taniguchi H., Okuma T., Kaai H., Anan M., Kakara Y., Doi M., Morishita S. Bull. Chem. Soc. Jpn. 66:1993;3712-3715
26. (b) Minisci F., Coppa F., Fontana F., Zhao L. Gazz. Chim. Ital. 123:1993;613-616.
27. (a) Kometani T., Kondo H., Fujimori Y. Synthesis. 1988;1005-1007
28. (b) Suzuki K., Matsumoto T., Hosoya T. J. Synth. Org. Chem. Jpn. 53:1995;1045-1054.
29. If not reduced in situ, 19 carrying a lower oxidation stage than that of 11, could not be obtained by the [5+2] process (Scheme 2). At least, reaction with 6 might involve the O→C process.
30. Similar bisnaphthols were obtained by employing electron donor-acceptor complexes. See: Okamoto I., Doi H., Kotani E., Takeya T. Tetrahedron Lett. 42:2001;2987-2989.
31. (a) Sartori G., Maggi R., Bigi F., Arienti A., Casnati G., Bocelli G., Mori G. Tetrahedron. 48:1992;9483-9494
32. (b) Sartori G., Maggi R., Bigi F., Arienti A., Casnati G. Tetrahedron Lett. 33:1992;2207-2210.
33. Iguchi M., Nishiyama A., Etoh H., Okamoto K., Yamamura S., Kato Y. Chem. Pharm. Bull. 34:1986;4910-4915.
34. From among several naphthol derivatives, only 1 satisfied the chemistry described in this article.