Domino 'Michael-retro-Michael-aldol' reactions of 1,3-bis-silyl enol ethers with 3-formylchromones

Tetrahedron Letters

Volumn 44, Issue 43, 2003, Pages 7921-7923

  Langer, Peter ^a   Appel, Bettina ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Benzophenones; Chromones; Cyclizations; Domino reactions; Silyl enol ethers

Indexed keywords

BENZOPHENONE DERIVATIVE; CHROMONE DERIVATIVE; ETHER DERIVATIVE;

ALDOL REACTION; ARTICLE; MICHAEL ADDITION; SYNTHESIS;

EID: 0141708685     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.008     Document Type: Article

References (42)

1. For salicylic esters and salicylic glycosides (e.g. salicortin), see for example: Römpp Lexikon Naturstoffe; Steglich, W.; Fugmann, B.; Lang-Fugmann, S., Eds.: Thieme, Stuttgart: 1997.
2. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
3. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
4. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
5. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
6. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
7. For anthracyclines, pyoluteorin, pyrrolomycines, anthranoids and their analogues, see: (a) Ezaki, N.; Shomura, T.; Koyama, M.; Niwa, T.; Kojima, M.; Inouye, S.; Niida, T. J. Antibiot. 1981, 34, 1363; (b) Kaneda, M.; Nakamura, S. ; Ezaki, N.; Iitaka, Y. J. Antibiot. 1981, 34, 1366; (c) Ezaki, N.; Koyama, M.; Shomura, T.; Tsuruoka, T.; Inouye, S. J. Antibiot. 1983, 36, 1263; (d) Carter, G. T.; Nietsche, J. A.; Goodman, J. J.; Torrey, M. J.; Dunne, T. S.; Siegel, M. M.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1271; (e) Müller, K. ; Leukel, P.; Ziereis, K.; Gawlik, I. J. Med. Chem. 1994, 37, 1660; (f) Barton, D. H. R.; Challis, J. A.; Magnus, P. D.; Marshall, J. P. J. Chem. Soc. (C) 1971, 2241.
8. Buchta E., Egger H. Chem. Ber. 90:1957;2760.
9. 2 mediated reaction of benzaldehydes with benzylhalides and subsequent oxidation, see: Shiue J.-S., Lin M.-H., Fang J.-M. J. Org. Chem. 62:1997;4643.
10. For the synthesis of salicylic esters from silyl enol ethers, see: (a) Chan, T. H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534; from 1,3-dicarbonyl dianions: (b) Harris, T. M.; Wittek, P. J. J. Am. Chem. Soc. 1975, 97, 3270; from alkynals and alkynones, see: (c) Covarrubias-Zúniga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688 and references cited therein.
11. For the synthesis of salicylic esters from silyl enol ethers, see: (a) Chan, T. H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534; from 1,3-dicarbonyl dianions: (b) Harris, T. M.; Wittek, P. J. J. Am. Chem. Soc. 1975, 97, 3270; from alkynals and alkynones, see: (c) Covarrubias-Zúniga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688 and references cited therein.
12. For the synthesis of salicylic esters from silyl enol ethers, see: (a) Chan, T. H.; Brownbridge, P. J. Am. Chem. Soc. 1980, 102, 3534; from 1,3-dicarbonyl dianions: (b) Harris, T. M.; Wittek, P. J. J. Am. Chem. Soc. 1975, 97, 3270; from alkynals and alkynones, see: (c) Covarrubias-Zúniga, A.; Ríos-Barrios, E. J. Org. Chem. 1997, 62, 5688 and references cited therein.
13. Langer P., Holtz E. Synlett. 2003;402.
14. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
15. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
16. For reviews of domino reactions, see: (a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131; (b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
17. These reagents can be regarded as masked 1,3-dicarbonyl dianions: (a) Chan, T.-H.; Brownbridge, P. J. Chem. Soc., Chem. Commun. 1979, 578; (b) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830.
18. These reagents can be regarded as masked 1,3-dicarbonyl dianions: (a) Chan, T.-H.; Brownbridge, P. J. Chem. Soc., Chem. Commun. 1979, 578; (b) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830.
19. Review: Langer P. Synthesis. 2002;441.
20. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
21. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
22. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
23. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
24. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
25. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
26. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
27. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
28. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
29. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
30. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
31. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
32. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
33. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
34. 2NOHHCl: (h) Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736; with o-phenylenediamine: (i) Ghosh, C. K.; Khan, S. Synthesis 1980, 701; for conversions into pyrroles and thiophenes: (j) Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133; for a review, see: (k) Ellis, G. P. Heterocyclic Compounds; Weisberger, A., Ed., 1977, 35, 921; see also: (l) Ghosh, C. K.; Ghosh, C. Ind. J. Chem. 1997, 36B, 968; for reactions with ketene acetals: (m) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293; with dienes: (n) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 58, 105; for the activation of chromones towards conjugate addition by the formation of silylated benzopyrylium triflates, see: (o) Lee, Y.-G.; Ishimaru, K.; Iwasaki, H.; Ohkata, K.; Akiba, K. J. Org. Chem. 1991, 56, 2058.
35. For other reactions of chromone derivatives from our laboratory, see: (a) synthesis of biaryl lactones: Langer, P.; Saleh, N. N. R.; Freifeld, I. Chem. Commun. 2002, 168; (b) synthesis of benzopyrano[2,3-b]pyridines: Langer, P.; Appel, B. Tetrahedron Lett. 2003, 44, 5133.
36. For other reactions of chromone derivatives from our laboratory, see: (a) synthesis of biaryl lactones: Langer, P.; Saleh, N. N. R.; Freifeld, I. Chem. Commun. 2002, 168; (b) synthesis of benzopyrano[2,3-b]pyridines: Langer, P.; Appel, B. Tetrahedron Lett. 2003, 44, 5133.
37. The reaction of 3-formylchromone with 1,3-dicarbonyl compounds has been reported to result in attack of the central carbon atom of the nucleophile onto the aldehyde (aldol condensation) and formation of open-chain products: (a) Ghosh, C. K.; Khan, S. Synthesis 1981, 903; (b) Hass, G.; Stanton, J. L.; von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607; (c) Prousek, J. Coll. Czech. Chem. Commun. 1991, 1361; (d) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Ind. J. Chem. Sect. B 1990, 29, 814; a cyclization with ring opening of the chromone system was observed only in specific cases: (e) Bandyopadhyay, C.; Sur, K. R.; Patra, R. J. Chem. Res. (S) 1998, 12, 802.
38. The reaction of 3-formylchromone with 1,3-dicarbonyl compounds has been reported to result in attack of the central carbon atom of the nucleophile onto the aldehyde (aldol condensation) and formation of open-chain products: (a) Ghosh, C. K.; Khan, S. Synthesis 1981, 903; (b) Hass, G.; Stanton, J. L.; von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607; (c) Prousek, J. Coll. Czech. Chem. Commun. 1991, 1361; (d) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Ind. J. Chem. Sect. B 1990, 29, 814; a cyclization with ring opening of the chromone system was observed only in specific cases: (e) Bandyopadhyay, C.; Sur, K. R.; Patra, R. J. Chem. Res. (S) 1998, 12, 802.
39. The reaction of 3-formylchromone with 1,3-dicarbonyl compounds has been reported to result in attack of the central carbon atom of the nucleophile onto the aldehyde (aldol condensation) and formation of open-chain products: (a) Ghosh, C. K.; Khan, S. Synthesis 1981, 903; (b) Hass, G.; Stanton, J. L.; von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607; (c) Prousek, J. Coll. Czech. Chem. Commun. 1991, 1361; (d) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Ind. J. Chem. Sect. B 1990, 29, 814; a cyclization with ring opening of the chromone system was observed only in specific cases: (e) Bandyopadhyay, C.; Sur, K. R.; Patra, R. J. Chem. Res. (S) 1998, 12, 802.
40. The reaction of 3-formylchromone with 1,3-dicarbonyl compounds has been reported to result in attack of the central carbon atom of the nucleophile onto the aldehyde (aldol condensation) and formation of open-chain products: (a) Ghosh, C. K.; Khan, S. Synthesis 1981, 903; (b) Hass, G.; Stanton, J. L.; von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607; (c) Prousek, J. Coll. Czech. Chem. Commun. 1991, 1361; (d) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Ind. J. Chem. Sect. B 1990, 29, 814; a cyclization with ring opening of the chromone system was observed only in specific cases: (e) Bandyopadhyay, C.; Sur, K. R.; Patra, R. J. Chem. Res. (S) 1998, 12, 802.
41. The reaction of 3-formylchromone with 1,3-dicarbonyl compounds has been reported to result in attack of the central carbon atom of the nucleophile onto the aldehyde (aldol condensation) and formation of open-chain products: (a) Ghosh, C. K.; Khan, S. Synthesis 1981, 903; (b) Hass, G.; Stanton, J. L.; von Sprecher, A.; Wenk, P. J. Heterocycl. Chem. 1981, 18, 607; (c) Prousek, J. Coll. Czech. Chem. Commun. 1991, 1361; (d) Ghosh, C. K.; Bandyopadhyay, C.; Biswas, S.; Chakravarty, A. K. Ind. J. Chem. Sect. B 1990, 29, 814; a cyclization with ring opening of the chromone system was observed only in specific cases: (e) Bandyopadhyay, C.; Sur, K. R.; Patra, R. J. Chem. Res. (S) 1998, 12, 802.
42. 4 (256.1): C 70.31, H 4.72; found C 70.04, H 4.89. All new compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.