A novel synthesis of 2-functionalized benzofurans by palladium-catalyzed cycloisomerization of 2-(1-hydroxyprop-2-ynyl)phenols followed by acid-catalyzed allylic isomerization or allylic nucleophilic substitution

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7336-7341

  Gabriele, Bartolo ^a   Mancuso, Raffaella ^a   Salerno, Giuseppe ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; ELECTRON TRANSITIONS; ISOMERIZATION; ISOMERS; PALLADIUM; PHENOLS;

2-METHYLENE; ACID-CATALYZED ISOMERIZATION; BASIC CONDITIONS; BENZOFURANS; CATALYTIC AMOUNTS; CHEMICAL EQUATIONS; CYCLOISOMERIZATION; FUNCTIONALIZED; NUCLEOPHILIC SUBSTITUTIONS; TWO-STEP SYNTHESIS;

SYNTHESIS (CHEMICAL);

2 (1 HYDROXYPROP 2 YNYL)PHENOL DERIVATIVE; 2 BUTOXYMETHYLBENZOFURAN; 2 HYDROXYMETHYLBENZOFURAN; 2 METHYLENE 2,3 DIHYDROBENZOFURAN 3 OL; ALLYL COMPOUND; BENZOFURAN DERIVATIVE; CHLORIDE; FURTRETHONIUM IODIDE; HYDROGEN SULFIDE; IODINE; PALLADIUM; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ISOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

ACIDS; ALLYL COMPOUNDS; BENZOFURANS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM; PHENOLS; STEREOISOMERISM;

EID: 52449131351     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801444n     Document Type: Article

References (123)

1. For recent examples, see: (a) Schultz, D. M.; Prescher, J. A.; Kidd, S.; Marona-Lewicka, D.; Nichols, D. E.; Monte, A. Bioorg. Med. Chem. 2008, 16, 6242-6251.
2. (b) Rizzo, S.; Riviere, C.; Piazzi, L.; Bisi, A.; Gobbi, S.; Bartolini, M.; Andrisano, V.; Morroni, F.; Tarozzi, A.; Monti, J.-P.; Rampa, A. J. Med. Chem. 2008, 51, 2883-2886.
3. (c) Kirilmis, C.; Ahmedzade, M.; Servi, S.; Koca, M.; Kizirgil, A.; Kazaz, C. Eur. J. Med. Chem. 2008, 43, 300-308.
4. (d) Ando, K.; Kawamura, Y.; Akai, Y.; Kunitomo, J.; Yokomizo, T.; Yamashita, M.; Ohta, S.; Ohishi, T.; Ohishi, Y. Org. Biomol. Chem. 2008, 6, 296-307.
5. (e) Ettaoussi, M.; Peres, B.; Klupsch, D.; Delagrange, P.; Boutin, J.-A.; Renard, P.; Caignard, D.-H.; Chavatte, P.; Berthelot, P.; Lesieur, D.; Yous, S. Bioorg. Med. Chem. 2008, 16, 4954-4962.
6. (f) Lee, Y.-K.; Woo, M.-H.; Kim, C.-H.; Kim, Y.; Lee, S.-H.; Jeong, B.-S.; Chang, H.-W.; Son, J.-K. Planta Med. 2007, 73, 1287-1291.
7. (g) Oda, K.; Yamaguchi, Y.; Yoshimura, T.; Wada, K.; Nishizono, N. Chem. Pharm. Bull. 2007, 55, 1419-1421.
8. (h) Filzen, G. F.; Bratton, L.; Cheng, X.-M.; Erasga, N.; Geyer, A.; Lee, C.; Lu, G.; Pulaski, J.; Sorenson, R. J.; Unangst, P. C.; Trivedi, B. K.; Xu, X. Bioorg. Med. Chem. Lett. 2007, 17, 3630-3635.
9. (i) Cowart, M.; Gfesser, G. A.; Browman, K. E.; Faghih, R.; Miller, T. R.; Milicic, I.; Baranowski, J. L.; Krueger, K. M.; Witte, D. G.; Molesky, A. L.; Komater, V. A.; Buckley, M. J.; Diaz, G. J.; Gagne, G. D.; Zhou, D.; Deng, X.; Pan, L.; Roberts, E. M.; Diehl, M. S.; Wetter, J. M.; Marsh, K. C.; Fox, G. B.; Brioni, J. D.; Esbenshade, T. A.; Hancock, A. A. Biochem. Pharmacol. 2007, 73, 1243-1255.
10. (j) Dixit, M.; Tripathi, B. K.; Tamrakar, A. K.; Srivastava, A. K.; Kumar, B.; Goel, A. Bioorg. Med. Chem. 2007, 15, 727-734.
11. (k) Ohishi, Y. Mol. Cancer Ther. 2007, 6, 3605S-3605S.
12. (l) Sakata, Y.; Kuramoto, M.; Ando, K.; Yamaguchi, M.; Kawasaki, I.; Kunitomo, J.; Yokomizo, T.; Ohishi, Y. Org. Biomol. Chem. 2007, 5, 3083-3086.
13. (m) Mahboobi, S.; Uecker, A.; Cenac, C.; Sellmer, A.; Eichhorn, E.; Elz, S.; Boehmer, F.-D.; Dove, S. Bioorg. Med Chem. 2007, 15, 2187-2197.
14. (n) Yang, H.; Pang, J.-Y.; Cai, Y.-Cl; Xu, Z.-L.; Xian, L.-J. J. Pharm. Pharmacol. 2006, 58, 1281-1287.
15. (o) Rida, S. M.; El-Hawash, S. A. M.; Fahmy, H. T. Y.; Hazzaa, A. A.; El-Meligy, M. M. M. Arch. Pharm. Res. 2006, 29, 826-833.
16. (p) Miklya, I. Int. J. Neuropsychopharmacol. 2006, 9, S197-S197.
17. (q) Takahata, K.; Tsunekawa, H.; Hirami, C.; Yoshimi, K.; Shimazu, S.; Yoneda, F.; Katsuki, H.; Akaike, A. Neurosci. Res. 2006, 55, S117-S117.
18. (r) Useglio, M.; Castellano, P. M.; Operto, M. A.; Torres, R.; Kaufman, T. S. Bioorg. Med. Chem. Lett. 2006, 16, 5097-5101.
19. (s) Patel, H. J.; Sarra, J.; Caruso, F.; Rossi, M.; Doshi, U.; Stephani, R. A. Bioorg. Med. Chem. Lett. 2006, 16, 4644-4637.
20. (t) Lazo, J. S.; Nunes, R.; Skoko, J. J.; de Oliveira, P. E. Q.; Vogt, A.; Wipf, P. Bioorg. Med. Chem. 2006, 14, 5643-5650.
21. (u) Gundogdu-Karaburun, N.; Benkli, K.; Tunali, Y.; Ucucu, U.; Demirayak, S. Eur. J. Med. Chem. 2006, 41, 651-656.
22. (v) Pautus, S.; Yee, S. W.; Jayne, M.; Coogan, M. P.; Simons, C. Bioorg. Med. Chem. 2006, 14, 3643-3653.
23. (w) Dawood, K. M.; Abdel-Gawad, H.; Ellithey, M.; Mohamed, H. A.; Hezagi, B. Arch. Pharm. 2006, 339, 133-140.
24. (x) Ahmad, G.; Mishra, P. K.; Gupta, P.; Yadav, P. P.; Tiwari, P.; Tamrakar, A. K.; Srivastava, A. K.; Maurya, R. Bioorg. Med. Chem. Lett. 2006, 16, 2139-2143.
25. (y) Ujjinamatada, R. K.; Appala, R. S.; Agasimundin, Y. S. J. Heterocycl. Chem. 2006, 43, 437-441.
26. (z) Saberi, M. R.; Vinh, T. K.; Yee, S. W.; Griffiths, B. J. N.; Evans, P. J.; Simons, C. J. Med. Chem. 2006, 49, 1016-1022.
27. (aa) Rida, S. M.; El-Hawash, S. A. M.; Fahmy, H. T. Y.; Hazza, A. A.; El-Meligy, M. M. M. Arch. Pharm. Res. 2006, 29, 16-25.
28. (bb) Gopalsamy, A.; Aplasca, A.; Ciszewski, G.; Park, K.; Ellingobe, J. W.; Orlowski, M.; Feld, B.; Howe, A. Y. M. Bioorg. Med. Chem. Lett. 2006, 16, 457-460.
29. (cc) Caijo, F.; Mosset, P.; Gree, R.; Chomarat, P.; Audinot-Bouchez, V.; Boutin, J.; Renard, P.; Caignard, D. H.; Dacquet, C. Lett. Org. Chem. 2006, 3, 103-106.
30. (dd) Khan, M. W.; Alam, M. J.; Rashid, M. A.; Chowdhury, R. Bioorg. Med. Chem. 2005, 13, 4796-4805.
31. For recent advances in the synthesis of benzofuran derivatives, see: (a) Sakai, N.; Uchida, N.; Konakahara, T. Tetrahedron Lett. 2008, 49, 3437-3440.
32. (b) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron 2008, 64, 53-60.
33. (c) Huang, X.-C.; Liu, Y. L.; Liang, Y.; Pi, S.-F.; Wang, F.; Li, J.-H. Org. Lett. 2008, 10, 1525-1528.
34. (d) Nakamura, I.; Mizushima, Y.; Yamagishi, U.; Yamamoto, Y. Tetrahedron 2007, 63, 8670-8676.
35. (e) Rasool, N.; Rashid, M. A.; Reinke, H.; Fischer, C.; Langer, P. Tetrahedron 2007, 63, 11626-11635.
36. (f) Witayakran, S.; Gelbaum, L.; Ragauskas, A. J. Tetrahedron 2007, 63, 10958-10962.
37. (g) Tadd, A. C.; Fielding, M. R.; Willis, M. C. Tetrahedron Lett. 2007, 48, 7578-7581.
38. (h) Bekassy, S.; Agai, B.; Farkas, J.; Gabor, E.; Ferenczi, M.; Figueras, F. Catal. Lett. 2007, 118, 219-223.
39. (i) Fakhari, A. R.; Nematollahi, D.; Shamsipur, M.; Makarem, S.; Davarani, S. S. H.; Alizadeh, A.; Khavasi, H. R. Tetrahedron 2007, 63, 3894-3898.
40. (j) Salih, K. S. M.; Ayoub, M. T.; Saadeh, H. A.; Al-Masoudi, N. A.; Mubarak, M. S. Heterocycles 2007, 71, 1577-1587.
41. (k) Nagamochi, M.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2007, 9, 2955-2958.
42. (l) Rafiee, M.; Nematollahi, D. Chem. Pharm. Bull. 2007, 55, 915-917.
43. (m) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361-2364.
44. (n) De Luca, L.; Giacomelli, G.; Nieddu, G. J. Org. Chem. 2007, 72, 3955-3957.
45. (o) Mattson, A. E.; Scheldt, K. A. J. Am. Chem. Soc. 2007, 129, 4508-4509.
46. (p) Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 149, 1-1509.
47. (q) Rao, M. L. N.; Awasthi, D. K.; Banerjee, D. Tetrahedron Lett. 2007, 48, 431-434.
48. (r) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. J. Org. Chem. 2007, 72, 9278-9282.
49. (s) Zhao, B.; Lu, X. Org. Lett. 2006, 8, 5987-5990.
50. (t) Santamaria, A.; Moreno-Manas, M.; Pleixats, R. Arkivoc 2007, 234-250.
51. (u) Ackermann, L.; Kaspar, L. T. J. Org. Chem. 2007, 72, 6149-6153.
52. (v) Jung, I.; Lee, J. K.; Song, K. H.; Song, K.; Kang, S. O.; Ko, J. J. Org. Chem. 2007, 72, 3652-3658.
53. (w) Bernini, R.; Cacchi, S.; De Salve, I.; Fabrizi, G. Synthesis 2007, 873-882.
54. (x) Capozzo, M.; D'Auria, M.; Emanuele, L.; Racioppi, R. J. Photochem. Photobiol. A 2007, 185, 38-43.
55. (y) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694-10695.
56. (z) Barluenga, J.; Vazquez-Villa, H.; Merino, I.; Ballesteros, A.; Gonzalez, J. M. Chem. Eur. J. 2006, 12, 5790-5805.
57. (aa) Dixit, M.; Sharon, A.; Maulik, P. R.; Goel, A. Synlett 2006, 1497-1502.
58. (bb) Kumar, M. P.; Liu, R. S. J. Org. Chem. 2006, 71, 4951-4955.
59. (cc) Aslam, S. N.; Stevenson, P. C.; Phythian, S. J.; Veitch, N. C.; Hall, D. R. Tetrahedron 2006, 62, 4214-4226.
60. (dd) Willis, M. C.; Taylor, D.; Gillmore, A. T. Tetrahedron 2006, 62, 11513-11520.
61. (ee) Sanz, R.; Miguel, D.; Martinez, A.; Perez, A. J. Org. Chem. 2006, 71, 4024-4027.
62. (ff) Pei, L. X.; Li, Y. M.; Bu, X. Z.; Gu, L. Q.; Chan, A. S. C. Tetrahedron Lett. 2006, 47, 2615-2618.
63. (gg) Carrill, M.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2006, 8, 1467-1470.
64. (hh) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Curr. Org. Chem. 2006, 10, 1423-1455.
65. (ii) Gabriele, B.; Mancuso, R.; Salerno, G.; Costa, M. Adv. Synth. Catal. 2006, 348, 1101-1109.
66. (jj) Radl, S.; Obadalova, I. Akivoc 2005, 4-11.
67. (kk) Bellur, E.; Langer, P. J. Org. Chem. 2005, 70, 10013-10029.
68. (ll) Yao, T. L.; Yue, D. W.; Larock, R. C. J. Comb. Chem. 2005, 7, 809-812.
69. (mm) Lu, K.; Luo, T. P.; Xiang, Z.; You, Z. J.; Fathi, R.; Chen, J. H.; Yang, Z. J. Comb. Chem. 2005, 7, 958-967.
70. (nn) Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022-15023.
71. (oo) Cruz, M. D.; Tamariz, J. Tetrahedron 2005, 61, 10061-10072.
72. (pp) Bellur, E.; Langer, P. J. Org. Chem. 2005, 70, 7686-7693.
73. (qq) Namatollahi, D.; Rafiee, M. Green Chem. 2005, 7, 638-644.
74. (rr) Van Otterlo, W. A. L.; Morgans, G. L.; Madeley, L. G.; Kuzvidza, S.; Moleele, S. S.; Thornton, N.; de Koning, C. B. Tetrahedron 2005, 61, 7746-7755.
75. (ss) Bellur, E.; Freifeld, I.; Langer, P. Tetrahedron Lett. 2005, 46, 2185-2187.
76. (tt) Barluenga, J.; Vazquez-Villa, H.; Ballesteros, A.; Gonzalez, J. M. Adv. Synth. Catal. 2005, 347, 526-530.
77. Kim, K. O.; Tae, J. Synthesis 2005, 387-390.
78. (uu) Yue, D. W.; Yao, T. L.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296.
79. (vv) Chen, C. Y.; Dormer, P. G. J. Org. Chem. 2005, 70, 6964-6967.
80. (ww) Colobert, F.; Castanet, A. S.; Abillard, O. Eur. J. Org. Chem. 2005, 3334-3341.
81. (xx) Sanz, R.; Castroviejo, M. P.; Fernandez, Y.; Fananas, F. J. J. Org. Chem. 2005, 70, 6548-6551.
82. (yy) Gabriele, B.; Mancuso, R.; Salerno, G.; Veltri, L. Chem. Commun. 2005, 271-273.
83. We have recently shown that PdI2 in conjunction with an excess of KI is an excellent catalyst for the heterocyclization of several acetylenic substrates bearing a suitably placed nucleophilic group. See ref 2r, ii, yy and: (a) Gabriele, B.; Mancuso, R.; Salerno, G.; Lupinacci, E.; Ruffolo, G.; Costa, M. J. Org. Chem. 2008, 73, 4971-4977.
84. (b) Gabriele, B.; Mancuso, R.; Salerno, G.; Plastina, P. J. Org. Chem. 2008, 73, 756-759.
85. (c) Plastina, P.; Gabriele, B.; Salerno, G. Synthesis 2007, 3083-3087.
86. (d) Gabriele, B.; Mancuso, R.; Salerno, G.; Ruffolo, G.; Plastina, P. J. Org. Chem. 2007, 72, 6873-6877.
87. (e) Gabriele, B.; Plastina, P.; Salerno, G.; Mancuso, R.; Costa, M. Org. Lett. 2007, 9, 3319-3322.
88. 2. In e-EROS, Electronic Encyclopedia of Reagents for Organic Synthesis; Crich, D., Ed.; Wiley-lnterscience: New York, 2006.
89. (g) Gabriele, B.; Plastina, P.; Salerno, G.; Mancuso, R. Synthesis 2006, 4247-4251.
90. (h) Gabriele, B.; Salerno, G.; Fazio, A.; Veltri, L. Adv. Synth. Catal. 2006, 348, 2212-2222.
91. (i) Gabriele, B.; Salerno, G.; Veltri, L.; Mancuso, R.; Li, Z.; Crispini, A.; Bellusci, A. J. Org. Chem. 2006, 71, 7895-7898.
92. (j) Bacchi, A.; Costa, M.; Delia Cà, N.; Gabriele, B.; Salerno, G.; Cassoni, S. J. Org. Chem. 2005, 70, 4971-1979.
93. (k) Gabriele, B.; Plastina, P.; Salerno, G.; Costa, M. Synlett 2005, 935-938.
94. (l) Gabriele, B.; Salerno, G.; Costa, M. Synlett 2004, 2468-2483.
95. (m) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. Curr. Org. Chem. 2004, 8, 919-946.
96. (n) Gabriele, B.; Salerno, G.; Plastina, P. Lett. Org. Chem. 2004, 1, 134-136.
97. (o) Costa, M.; Delia Cà, N.; Gabriele, B.; Massera, C.; Salerno, G.; Soliani, M. J. Org. Chem. 2004, 69, 2469-2477.
98. (p) Gabriele, B.; Salerno, G.; Plastina, P.; Costa, M.; Crispini, A. Adv. Synth. Catal. 2004, 346, 351-358.
99. (q) Bacchi, A.; Costa, M.; Delia Cà, N.; Fabbricatore, M.; Fazio, A.; Gabriele, B.; Nasi, C.; Salerno, G. Eur. J. Org. Chem. 2004, 57, 4-585.
100. (r) Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 2003, 687, 219-228.
101. (s) Gabriele, B.; Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853-7861.
102. (t) Chiusoli, G. P.; Costa, M.; Cucchia, L.; Gabriele, B.; Salerno, G.; Veltri, L. J. Mol. Catal. A: Chem. 2003, 204, 133-142.
103. (u) Gabriele, B.; Salerno, G.; Fazio, A.; Pittelli, R. Tetrahedron 2003, 59, 6251-6259.
104. (v) Bacchi, A.; Costa, M.; Gabriele, B.; Pelizzi, G.; Salerno, G. J. Org. Chem. 2002, 67, 4450-4457.
105. (w) Gabriele, B.; Salerno, G.; Fazio, A.; Campana, F. B. Chem. Commun. 2002, 1408-1409.
106. (x) Gabriele, B.; Salerno, G.; Veltri, L.; Costa, M.; Massera, C. Eur. J. Org. Chem. 2001, 460, 7-4613.
107. (y) Gabriele, B.; Salerno, G.; Fazio, A.; Bossio, M. R. Tetrahedron Lett. 2001, 42, 1339-1341.
108. (z) Gabriele, B.; Salerno, G.; Fazio, A. Org. Lett. 2000, 2, 351-352.
109. (aa) Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 2000, 593, 409-415.
110. (bb) Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M.; Chiusoli, G. P. J. Org. Chem. 1999, 64, 7693-7699.
111. (cc) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687-7692.
112. (dd) Chiusoli, G. P.; Costa, M.; Gabriele, B.; Salerno, G. J. Mol. Catal. A: Chem. 1999, 143, 297-310.
113. (ee) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Sani, C.; Gabriele, B.; Salerno, G. J. Organomet. Chem. 1998, 562, 35-43.
114. (ff) Gabriele, B.; Salerno, G.; De Pascali, F.; Tomasi Scianò, G.; Costa, M.; Chiusoli, G. P. Tetrahedron Lett. 1997, 38, 6877-6880.
115. (gg) Bacchi, A.; Chiusoli, G. P.; Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209-1210.
116. (hh) Gabriele, B.; Salerno, G. Chem. Commun. 1997, 1083-1084.
117. (ii) Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1997, 147-154.
118. (jj) Bonardi, A.; Costa, M.; Gabriele, B.; Salerno, G.; Chiusoli, G. P. Tetrahedron Lett. 1995, 36, 7495-7498.
119. (kk) Gabriele, B.; Costa, M.; Salerno, G.; Chiusoli, G. P. J. Chem. Soc., Chem. Commun. 1994, 1429-1430.
120. The methodology could not be applied to alcohols of low nucleophilicity, such as isopropyl alcohol (R = i-Pr) or tert-butylalcohol (R = t-Bu), or to phenols (R = Ar); in these cases, the GLC, GLC-MS, and TLC analyses of the reaction crudes showed that substrates 2 preferentially underwent decomposition, with formation of small amounts of the desired products, which, however, owing to the complexity of the mixture, could not be isolated at the pure state.
121. 2-promoted deprotection of the corresponding methylthiomethyl ether) by classical intramolecular conjugate addition to give a mixture of (3-hydroxy-3-methyl-3H-benzofuran-2-ylidene) acetic acid ethyl ester (15%) and hydroxy-(3-methylbenzofuran-2-yl)acetic acid ethyl ester (68%) was reported some years ago. Pflieger, D.; Muckensturm, B. Tetrahedron 1989, 45, 2031-2040.
122. +], 161 (13), 160 (87), 145 (7), 132 (21), 118 (16), 117 (41), 103 (30), 102 (43), 89 (100), 77 (22), 63 (59), 62 (23), 53 (33), 51 (22).
123. Baciocchi, E.; Clementi, S.; Sebastiani, V. J. Chem. Soc., Perkin Trans. 2 1974, 1882-1884.