A new strategy for the synthesis of chromans and chromenes

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5105-5108

  Knight, David W ^a   Little, Paul B ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Arynes; Chromans; Sonogashira; Trapping reactions

Indexed keywords

ALCOHOL DERIVATIVE; ALKANOL; ALKENE; ALKYNE; BENZENE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE; CHROMAN DERIVATIVE; CHROMENE DERIVATIVE; IODINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; REDUCTION; SPIN TRAPPING; SYNTHESIS;

EID: 0032500086     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00937-X     Document Type: Article

References (16)

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2. 1. Campbell, C.D. and Rees, C.W. J. Chem. Soc. (C), 1969, 742, 748 and 752; for a review of benzyne chemistry in general, see Kessar, S. V. Comp. Org. Synth., eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, 4, 483, and references therein.
3. 2. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6935; Li, S.K.Y.; Knight, D.W. and Little, P.B. Tetrahedron Lett., 1996, 37, 5615. For a review of lateral metallation directed by NBoc groups, see Clark, R.D. and Jahangir, A. Org. React., 1995, 47, 1. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem., 1986, 51, 979; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem., 1989, 59, 4019.
4. 2. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6935; Li, S.K.Y.; Knight, D.W. and Little, P.B. Tetrahedron Lett., 1996, 37, 5615. For a review of lateral metallation directed by NBoc groups, see Clark, R.D. and Jahangir, A. Org. React., 1995, 47, 1. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem., 1986, 51, 979; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem., 1989, 59, 4019.
5. 2. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6935; Li, S.K.Y.; Knight, D.W. and Little, P.B. Tetrahedron Lett., 1996, 37, 5615. For a review of lateral metallation directed by NBoc groups, see Clark, R.D. and Jahangir, A. Org. React., 1995, 47, 1. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem., 1986, 51, 979; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem., 1989, 59, 4019.
6. 2. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6935; Li, S.K.Y.; Knight, D.W. and Little, P.B. Tetrahedron Lett., 1996, 37, 5615. For a review of lateral metallation directed by NBoc groups, see Clark, R.D. and Jahangir, A. Org. React., 1995, 47, 1. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem., 1986, 51, 979; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem., 1989, 59, 4019.
7. 2. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6935; Li, S.K.Y.; Knight, D.W. and Little, P.B. Tetrahedron Lett., 1996, 37, 5615. For a review of lateral metallation directed by NBoc groups, see Clark, R.D. and Jahangir, A. Org. React., 1995, 47, 1. For preparations of other substituted aminobenzotriazoles, see, for example, Hart, H.; Ok, D. J. Org. Chem., 1986, 51, 979; Rigby, J. H.; Holsworth, D. D.; James, K. J. Org. Chem., 1989, 59, 4019.
8. 3. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6939; Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Synlett., 1994, 253.
9. 3. Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Tetrahedron Lett., 1993, 34, 6939; Birkett, M.A.; Knight, D.W. and Mitchell, M.B. Synlett., 1994, 253.
10. 4. Knight, D. W. Comp. Org. Synth., eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, 3, 481.
11. 5. Knight D. W. and Little, P. B. Tetrahedron Lett., 1997, 38, 5037.
12. 6. Sonogashira, K. Comp. Org. Synth., eds. Trost, B. M.; Fleming, I. Pergamon Press, Oxford, 1991, 3, 521.
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15. 8. Rieke, R. D.; Li, P. T-J.; Burns, T. P.; Uhm, S. T. J. Org. Chem., 1981, 46, 4323; Chou, W-N.; Clark, D. L.; White, J. B. Tetrahedron Lett., 1991, 32, 299 and references therein.
16. 9. For a recently reported alternative approach to chromenes, see Pelter, A.; Hussain, A.; Smith, G.; Ward, R. S. Tetrahedron, 1997, 53, 3879.