A new approach to dihydrobenzofurans and dihydrobenzopyrans (chromans) based on the intramolecular trapping by alcohols of benzynes generated from 7-substituted-1-aminobenzotriazoles

Tetrahedron

Volumn 56, Issue 7, 2000, Pages 1013-1023

  Birkett, Michael A ^a   Knight, David W ^b   Little, Paul B ^b   Mitchell, Michael B ^c  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c SB Pharmaceuticals   (United Kingdom)

Author keywords

Alcohols; Arynes; Benzofurans; Intramolecular trapping

Indexed keywords

BENZENE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CHROMAN DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0034635457     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00021-1     Document Type: Article

References (41)

1. Hoffmann, R. W. Dehydrobenzenes, Cycloalkynes; Academic Press: New York, 1967; Sharp, J. T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 1, p. 477; Rienecke, M. G. Tetrahedron 1982, 38, 427; Moody, C. J.; Whitham, G. H. Reactive Intermediates; Oxford University Press: Oxford, 1992 and references cited therein.
2. Hoffmann, R. W. Dehydrobenzenes, Cycloalkynes; Academic Press: New York, 1967; Sharp, J. T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 1, p. 477; Rienecke, M. G. Tetrahedron 1982, 38, 427; Moody, C. J.; Whitham, G. H. Reactive Intermediates; Oxford University Press: Oxford, 1992 and references cited therein.
3. Hoffmann, R. W. Dehydrobenzenes, Cycloalkynes; Academic Press: New York, 1967; Sharp, J. T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 1, p. 477; Rienecke, M. G. Tetrahedron 1982, 38, 427; Moody, C. J.; Whitham, G. H. Reactive Intermediates; Oxford University Press: Oxford, 1992 and references cited therein.
4. Hoffmann, R. W. Dehydrobenzenes, Cycloalkynes; Academic Press: New York, 1967; Sharp, J. T. In Comprehensive Organic Chemistry; Barton, D. H. R., Ollis, W. D., Eds.; Pergamon: Oxford, 1979; Vol. 1, p. 477; Rienecke, M. G. Tetrahedron 1982, 38, 427; Moody, C. J.; Whitham, G. H. Reactive Intermediates; Oxford University Press: Oxford, 1992 and references cited therein.
5. Kessar S.V. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 4:1991;483 Pergammon, Oxford.
6. Campbell, C. D.; Rees, C. W.; J. Chem. Soc (C) 1969, 742, 748 and 752; See also Fleet, G. W. J.; Fleming, I. J. Chem. Soc (C), 1969, 1758.
7. Campbell, C. D.; Rees, C. W.; J. Chem. Soc (C) 1969, 742, 748 and 752; See also Fleet, G. W. J.; Fleming, I. J. Chem. Soc (C), 1969, 1758.
8. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
9. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
10. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
11. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
12. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
13. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem. 1986, 51, 979; Hart, H.; Lai, C-Y.; Nurukogu, G. C.; Shamoniken, S. Tetrahedron 1987, 43, 5203; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem. 1989, 59, 4019. For applications to the generation of 2,3-dihydronaphthalene and dehydrophenanthrene, see Hales, R. H.; Bradshaw, J. S.; Pratt, D. R. J. Org. Chem. 1971, 36, 314; Hales, R. H.; Bradshaw, J. S. J. Org. Chem. 1971, 36, 318; See also Rees, C. W.; Storr, R. C.; J. Chem. Soc. (C) 1969, 760.
14. Keating, M.; Peck, M. E.; Rees, C. W.; Storr, R. C. J. Chem. Soc., Perkin Trans. 1 1972, 1315; Graveling, F. Ph.D. thesis, University of Leicester, 1969.
15. Keating, M.; Peck, M. E.; Rees, C. W.; Storr, R. C. J. Chem. Soc., Perkin Trans. 1 1972, 1315; Graveling, F. Ph.D. thesis, University of Leicester, 1969.
16. Cadogan J.I.G., Thomson J.B. J. Chem. Soc., Chem. Commun. 1969;770.
17. Buente J.M., Castedo L., Rodriguez de Lera L., Saa J.M., Suau R., Vidal M.C. Tetrahedron Lett. 24:1993;2298.
18. Knight D.W., Little P.B. Synlett. 1998;1141.
19. For a review of lateral metallation directed by N-Boc groups, see Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1.
20. Birkett M.A., Giles R.G., Knight D.W., Mitchell M.B. J. Chem. Soc., Perkin Trans. 1. 1998;2301.
21. Masui Y., Chino N., Sawakibura S. Bull. Chem. Soc. Jpn. 53:1980;464. (and references therein).
22. Lundt B.F., Johansen N.L., Volund A., Markussen J. Int. J. Pept. Protein Res. 12:1978;258.
23. For preliminary reports on sections of this work, see Birkett, M. B.; Knight, D. W.; Mitchell, M. B. Tetrahedron Lett. 1993, 34, 6939; Synlett 1994, 253.
24. For preliminary reports on sections of this work, see Birkett, M. B.; Knight, D. W.; Mitchell, M. B. Tetrahedron Lett. 1993, 34, 6939; Synlett 1994, 253.
25. Kim K.M., Kim H.R., Ryu E.J.C. Heterocycles. 36:1993;497.
26. Houghton P.G., Rees C.W. J. Chem. Res. (S). 1980;303.
27. Günther H. NMR Spectroscopy. 2nd. ed. 1992;George Thieme, Stuttgart. (English translation).
28. McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422; Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508; Mitchell, T. N. Synthesis 1992, 803.
29. McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422; Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508; Mitchell, T. N. Synthesis 1992, 803.
30. McKean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422; Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508; Mitchell, T. N. Synthesis 1992, 803.
31. Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;521 Pergamon, Oxford.
32. Heck, R. F. Org. React. 1982, 27, 345; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p. 833; de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
33. Heck, R. F. Org. React. 1982, 27, 345; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p. 833; de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
34. Heck, R. F. Org. React. 1982, 27, 345; Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, p. 833; de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
35. Suzuki, A. Acc. Chem. Res. 1982, 15, 178; Pure Appl. Chem. 1991, 63, 419.
36. Suzuki, A. Acc. Chem. Res. 1982, 15, 178; Pure Appl. Chem. 1991, 63, 419.
37. Wittig, G.; Pohmer, L. Angew. Chem. 1956, 67, 348; Chem. Ber. 1956, 89, 1334.
38. Wittig, G.; Pohmer, L. Angew. Chem. 1956, 67, 348; Chem. Ber. 1956, 89, 1334.
39. Wolthuis, E.; Bouma, B.; Mudderman, J.; Sytsma, L. Tetrahedron Lett. 1970, 407; Pal, R. S.; Bohadia, M. M. Pol. J. Chem. 1978, 52, 1473.
40. Wolthuis, E.; Bouma, B.; Mudderman, J.; Sytsma, L. Tetrahedron Lett. 1970, 407; Pal, R. S.; Bohadia, M. M. Pol. J. Chem. 1978, 52, 1473.
41. Armarego W.L.F., Perrin D.D. Purification of Laboratory Chemicals. 1996;Butterworth Heinemann, Oxford.