Versatile synthesis of (Z)-1-alkylidene-1,3-dihydroisobenzofurans and 1H-isochromenes by palladium-catalyzed cycloisomerization of 2-alkynylbenzyl alcohols

Tetrahedron

Volumn 59, Issue 33, 2003, Pages 6251-6259

  Gabriele, Bartolo ^a   Salerno, Giuseppe ^a   Fazio, Alessia ^a   Pittelli, Rosina ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

1,3 dihydroisobenzofurans; Cycloisomerization; Isochromenes; Palladium

Indexed keywords

(2 HEX 1 YNYLPHENYL)METHANOL; 1 (2 HEX 1 YNYLPHENYL)PENTAN 1 OL; 1 (2 PHENYLETHYNYLPHENYL)PENTAN 1 OL; 1 BENZYLIDENE 3 BUTYL 1,3 DIHYDROISOBENZOFURAN; 1 BUTYL 3 PHENYL 1H ISOCHROMENE; 1,1 DIETHYL 3 PENTYLIDENE 1,3 DIHYDROISOBENZOFURAN; 1,3 DIBUTYL 1H ISOCHROMENE; 3 (2 HEX 1 YNYLPHENYL)PENTAN 3 OL; 3 (2 PHENYLETHYNYLPHENYL)PENTAN 3 OL; 3 BENZYLIDENE 1,1 DIETHYL 1,3 DIHYDROISOBENZOFURAN; 3 BUTYL 1,1 DIETHYL 1H ISOCHROMENE; 3 BUTYL 1H ISOCHROMENE; BENZYL ALCOHOL DERIVATIVE; CHROMENE DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; ISOBENZOFURAN DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; BIOAVAILABILITY; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; INFRARED SPECTROMETRY; ISOMERISM; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0042704939     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01019-6     Document Type: Article

References (46)

1. (a) Li J.J., Gribble G.W. Palladium in Heterocyclic Chemistry. 2000;Pergamon, Oxford.
2. (b) Negishi E. Handbook of Organopalladium Chemistry for Organic Synthesis. 2002;Wiley, New York.
3. (a) Gabriele B., Salerno G., Fazio A., Bossio M.R. Tetrahedron Lett. 42:2001;1339-1341.
4. (b) Gabriele B., Salerno G., Fazio A. Org. Lett. 2:2000;351-352.
5. (c) Gabriele B., Salerno G., Lauria E. J. Org. Chem. 64:1999;7687-7692.
6. (d) Gabriele B., Salerno G. Chem. Commun. 1997;1083-1084.
7. (a) Gabriele B., Salerno G., Fazio A., Campana F.B. Chem. Commun. 2002;1408-1409.
8. (b) Bacchi A., Costa M., Gabriele B., Pelizzi G., Salerno G. J. Org. Chem. 67:2002;4450-4457.
9. (c) Gabriele B., Salerno G., Veltri L., Costa M., Massera C. Eur. J. Org. Chem. 2001;4607-4613
10. (d) Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Organomet. Chem. 593-594:2000;409-415.
11. (e) Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Org. Chem. 64:1999;7693-7699.
12. (f) Chiusoli G.P., Costa M., Gabriele B., Salerno G. J. Mol. Catal. A: Chem. 143:1999;297-310.
13. (g) Bacchi A., Chiusoli G.P., Costa M., Sani C., Gabriele B., Salerno G. J. Organomet. Chem. 562:1998;35-43.
14. (h) Gabriele B., Salerno G., De Pascali F., Tomasi Scianò G., Costa M., Chiusoli G.P. Tetrahedron Lett. 38:1997;6877-6880.
15. (i) Bacchi A., Chiusoli G.P., Costa M., Gabriele B., Righi C., Salerno G. Chem. Commun. 1997;1209-1210
16. (j) Gabriele B., Salerno G., De Pascali F., Costa M., Chiusoli G.P. J. Chem. Soc., Perkin Trans. 1. 1997;147-154.
17. (k) Bonardi A., Costa M., Gabriele B., Salerno G., Chiusoli G.P. Tetrahedron Lett. 36:1995;7495-7498
18. (l) Gabriele B., Costa M., Salerno G., Chiusoli G.P. J. Chem. Soc., Chem. Commun. 1994;1429-1430.
19. Padwa A., Krumpe K.E., Weingarten M.D. J. Org. Chem. 60:1995;5595-5603.
20. Hiroya K., Jouka R., Kameda M., Yasuhara A., Sakamoto T. Tetrahedron. 57:2001;9697-9710.
21. Cu(I)-catalyzed cycloisomerization of 3-(2-hydroxymethylphenyl)-1-arylprop-2-yn-1-ols (formed in situ by Sonogashira coupling between 2-iodobenzylalcohol and 1-arylprop-2-yn-1-ols) to (E)-2-(3H-isobenzofuran-1-ylidene)-1-arylethanols has been reported: Khan M.W., Kundu N.G. Synlett. 1999;456-458. However, this reaction led to 1-alkylidene-1,3-dihydroisobenzofurans with E stereochemistry and did not work with simple alk-1-ynes.
22. Sammes P.G., Weller D.J. Synthesis. 1995;1205-1222.
23. For recent examples, see: (a) Nagao Y., Ueki A., Asano K., Tanaka S., Sano S., Shiro M. Org. Lett. 4:2002;455-457 (b) Antonioletti R., Bovicelli P., Crescenzi B., Lupattelli P. Tetrahedron Lett. 39:1998;6751-6752 (c) Azzena U., Demartis S., Fiori M.G., Melloni G., Pisano L. Tetrahedron Lett. 36:1995;8123-8126. For a recent study on the reductive cleavage of dihydroisobenzofurans and related synthetic applications, see: (d) Azzena U., Demartis S., Melloni G. J. Org. Chem. 61:1996;4913-4919.
24. For recent examples, see: (a) Nagao Y., Ueki A., Asano K., Tanaka S., Sano S., Shiro M. Org. Lett. 4:2002;455-457 (b) Antonioletti R., Bovicelli P., Crescenzi B., Lupattelli P. Tetrahedron Lett. 39:1998;6751-6752 (c) Azzena U., Demartis S., Fiori M.G., Melloni G., Pisano L. Tetrahedron Lett. 36:1995;8123-8126. For a recent study on the reductive cleavage of dihydroisobenzofurans and related synthetic applications, see: (d) Azzena U., Demartis S., Melloni G. J. Org. Chem. 61:1996;4913-4919.
25. For recent examples, see: (a) Nagao Y., Ueki A., Asano K., Tanaka S., Sano S., Shiro M. Org. Lett. 4:2002;455-457 (b) Antonioletti R., Bovicelli P., Crescenzi B., Lupattelli P. Tetrahedron Lett. 39:1998;6751-6752 (c) Azzena U., Demartis S., Fiori M.G., Melloni G., Pisano L. Tetrahedron Lett. 36:1995;8123-8126. For a recent study on the reductive cleavage of dihydroisobenzofurans and related synthetic applications, see: (d) Azzena U., Demartis S., Melloni G. J. Org. Chem. 61:1996;4913-4919.
26. For recent examples, see: (a) Nagao Y., Ueki A., Asano K., Tanaka S., Sano S., Shiro M. Org. Lett. 4:2002;455-457 (b) Antonioletti R., Bovicelli P., Crescenzi B., Lupattelli P. Tetrahedron Lett. 39:1998;6751-6752 (c) Azzena U., Demartis S., Fiori M.G., Melloni G., Pisano L. Tetrahedron Lett. 36:1995;8123-8126. For a recent study on the reductive cleavage of dihydroisobenzofurans and related synthetic applications, see: (d) Azzena U., Demartis S., Melloni G. J. Org. Chem. 61:1996;4913-4919.
27. For representative examples, see: (a) Martin C., Mailliet P., Maddaluno J. J. Org. Chem. 66:2001;3797-3805 (b) Meegalla S.K., Rodrigo R. J. Org. Chem. 56:1991;1882-1888 (c) Meegalla S.K., Rodrigo R. Synthesis. 1989;942-944.
28. For representative examples, see: (a) Martin C., Mailliet P., Maddaluno J. J. Org. Chem. 66:2001;3797-3805 (b) Meegalla S.K., Rodrigo R. J. Org. Chem. 56:1991;1882-1888 (c) Meegalla S.K., Rodrigo R. Synthesis. 1989;942-944.
29. For representative examples, see: (a) Martin C., Mailliet P., Maddaluno J. J. Org. Chem. 66:2001;3797-3805 (b) Meegalla S.K., Rodrigo R. J. Org. Chem. 56:1991;1882-1888 (c) Meegalla S.K., Rodrigo R. Synthesis. 1989;942-944.
30. See, for example: Brown D.S., Elliott M.C., Moody C.J., Mowlem T.J. J. Chem. Soc., Perkin Trans. 1. 1995;1137-1144.
31. For representative examples, see: (a) Michaelides M.R., Schoenleber R., Thomas S., Yamamoto D.M., Britton D.R., MacKenzie R., Kebabian J.W. J. Med. Chem. 34:1991;2946-2953 (b) DeNinno M.P., Schoenleber R., Perner R.J., Lijewski L., Asin K.E., Britton D.R., MacKenzie R., Kebabian J.W. J. Med. Chem. 34:1991;2561-2569.
32. For representative examples, see: (a) Michaelides M.R., Schoenleber R., Thomas S., Yamamoto D.M., Britton D.R., MacKenzie R., Kebabian J.W. J. Med. Chem. 34:1991;2946-2953 (b) DeNinno M.P., Schoenleber R., Perner R.J., Lijewski L., Asin K.E., Britton D.R., MacKenzie R., Kebabian J.W. J. Med. Chem. 34:1991;2561-2569.
33. See, for example: Kobayashi K., Konishi A., Kanno Y., Suginome H. J. Chem. Soc., Perkin Trans. 1. 1993;111-115.
34. See, for example: Xu Y.-C., Lebeau E., Gillard J.W., Attardo G. Tetrahedron Lett. 34:1993;3841-3844. and references cited therein.
35. Dopico P.G., Finn M.G. Tetrahedron. 55:1999;29-62.
36. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman Scientific and Technical: Essex, 1989; p 699.
37. Shi C., Zhang Q., Wang K.K. J. Org. Chem. 64:1999;925-932.
38. Zhang Q., Shi C., Zhang H.-R., Wang K.K. J. Org. Chem. 65:2000;7977-7983.
39. Wang X., Silverman R.B. J. Org. Chem. 63:1998;7357-7363.
40. Sashida H., Ohyanagi K., Minoura M., Akiba K. J. Chem. Soc., Perkin Trans. 1. 2002;606-612.
41. (a) Smith R.E., Richards N.G.J. J. Org. Chem. 62:1997;1183-1187.
42. (b) Begasse B., Hercouet A., Le Corre M. Tetrahedron Lett. 1979;2149-2150.
43. (a) Biagetti M., Bellina F., Carpita A., Stabile P., Rossi R. Tetrahedron. 58:2002;5023-5038.
44. (b) Kundu N.G., Pal M., Nandi B. J. Chem. Soc., Perkin Trans. 1. 1998;561-568.
45. (c) Kuro K., Foruune M., Enna M., Miura M., Nomura M. J. Org. Chem. 58:1993;4716-4721.
46. (d) Padwa A., Chiacchio U., Fairfax D.J., Kassir J.M., Litrico A., Semones M.A., Xu S.L. J. Org. Chem. 58:1993;6429-6437.