Synthesis of 3-aryl-2-arylamidobenzofurans based on the curtius rearrangement

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2502-2520

  Carrër, Amandine ^a,b   Florent, Jean Claude ^a,b   Auvrouin, Emilie ^d   Rousselle, Patricia ^c   Bertounesque, Emmanuel ^a,b  

^a CNRS   (France)

^b INSTITUT CURIE   (France)

^c INSTITUT DE BIOLOGIE ET CHIMIE DES PROTÉINES   (France)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACYL TRANSFER; AROYLATION; ARYL AMIDE; BENZOFURANS; N-ALKYLATION; NH GROUPS; ONE POT; REDUCTIVE DEBROMINATION; SUZUKI-MIYAURA CROSS-COUPLING;

CARBOXYLIC ACIDS;

CHEMICAL REACTIONS;

2 ARYLAMIDO 3 BROMOBENZOFURAN; 3 ARYL 2 ARYLAMIDOBENZOFURAN; BENZOFURAN DERIVATIVE; BENZYL 3 BROMOBENZOFURAN 2 YLCARBAMATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CONTROLLED STUDY; CURTIUS REARRANGEMENT; DEBROMINATION; DEHALOGENATION; ONE POT SYNTHESIS; SUZUKI REACTION; SYNTHESIS;

4-AMINOPYRIDINE; ALKYLATION; AMIDES; AMINES; BENZOFURANS; BIOLOGICAL PRODUCTS; BORONIC ACIDS; CARBOXYLIC ACIDS; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; STEREOISOMERISM;

EID: 79953905597     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102265b     Document Type: Article

References (115)

1. For reviews on benzo[ b ]furan-containing natural products, see: Donelly, D. M. X.; Meegan, M. J. Furans and Their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 657 - 712.
2. Cagniant, P.; Cagniant, D. Adv. Heterocycl. Chem. 1975, 18, 337-482
3. Bird, C. W.; Cheeseman, G. W. H. Synthesis of Five-membered Rings with One Heteroatom. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 89 - 153.
4. For selected recent synthesis of benzofuran-based natural products, see: Kraus, G. A.; Gupta, V. Tetrahedron Lett. 2009, 50, 7180-7183
5. Kraus, G. A.; Kim, I. Org. Lett. 2003, 5, 1191-1192
6. Kerr, D. J.; Willis, A. C.; Flynn, B. L. Org. Lett. 2004, 6, 457-460
7. For leading reviews on the biological activities of benzofurans, see: Ziegert, R. E.; Toraeng, J.; Knepper, K.; Braese, S. J. Comb. Chem. 2005, 7, 147-169
8. Hou, X.-L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. Prog. Heterocycl. Chem. 2005, 17, 142-171
9. Eissenstat, M. Patent WO 2008 115894.
10. Dai, J. R.; Hallock, J. H., II; Boyd, M. J. Nat. Prod. 1998, 67, 351-353
11. Gangjee, A.; Devraj, R.; McGuire, J. J.; Kisliuk, R. L. J. Med. Chem. 1995, 38, 3798-3805
12. Huang, H.-C.; Chamberlain, T. S.; Selbert, K.; Koboldt, C. M.; Isakson, P. C.; Reitz, D. B. Bioorg. Med. Chem. Lett. 1995, 5, 2377-2380
13. Shimazu, S.; Takahata, K.; Katsuki, H.; Tsunekawa, H.; Tanigawa, A.; Yoneda, F.; Knoll, J.; Akaike, A. Eur. J. Pharmacol. 2001, 421, 181-189
14. Singh, B. M.; Vaughan Williams, E. M. Br. J. Pharmacol. 1970, 139, 255-264
15. Ohemeng, K. A.; Apollina, M. A.; Nguyen, V. N.; Schwender, C. F.; Singer, M.; Steber, M.; Ansell, J.; Argentieri, D.; Hageman, W. J. Med. Chem. 1994, 37, 3663-3667
16. Kiyama, R.; Homna, T.; Hayashi, K.; Ogawa, M.; Hara, M.; Fujimoto, M.; Fujishita, T. J. Med. Chem. 1995, 38, 2728-2741
17. Kozikowsky, A. P.; Ma, D.; Du, L.; Lewin, N. E.; Blumberg, P. M. J. Am. Chem. Soc. 1995, 117, 6666-6672
18. Malamas, M. S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W.; McDevitt, R.; Adebayo, F. O.; Sawicki, D. R.; Seestaller, L.; Sullivan, D.; Taylor, J. R. J. Med. Chem. 2000, 43, 1293-1310
19. Na, M; Hoang, D. M.; Njamen, D.; Mbafor, J. T.; Fomum, Z. T.; Thuong, P. T.; Ahn, J. S.; Oh, W. K. Bioorg. Med. Chem. Lett. 2007, 17, 3868-3871
20. Dixit, M.; Tripathi, B. K.; Tamrakar, A. K.; Srivastava, A. K.; Kumar, B.; Goel, A. Bioorg. Med. Chem. 2007, 15, 727-734
21. Smith, R. A.; Chen, J.; Mader, M. M.; Muegge, I.; Moehler, U.; Katti, S.; Marrero, D.; Stirtan, W. G.; Weaver, D. R.; Xiao, H.; Carley, W. Bioorg. Med. Chem. Lett. 2002, 12, 2875-2878
22. Collini, M. D.; Kaufman, D. H.; Manas, E. S.; Harris, H. A.; Henderson, R. A.; Xu, Z. B.; Unwalla, R. J.; Miller, C. P. Bioorg. Med. Chem. Lett. 2004, 14, 4925-4929
23. Li, J.; Rush, T. S., III; Li, W.; DeVincentis, D.; Du, X.; Hu, Y.; Thomason, J. R.; Xiang, J. S.; Skotnicki, J. S.; Tam, S.; Cunningham, K. M.; Chockalingam, P. S.; Morris, E. A.; Levin, J. I. Bioorg. Med. Chem. Lett. 2005, 15, 4961-4966
24. Prashad, A. S.; Wang, D.; Subrath, J.; Wu, B.; Lin, M.; Zhang, M.-Y.; Kagan, N.; Lee, J.; Yang, X.; Brennan, A.; Chaudhary, D.; Xu, X.; Leung, L.; Wang, J.; Boschelli, D. H. Bioorg. Med. Chem. Lett. 2009, 19, 5799-5802
25. Cowart, M.; Pratt, J. K.; Stewart, A. O.; Bennani, Y. L.; Esbenshade, T. A.; Hancock, A. A. Bioorg. Med. Chem. Lett. 2004, 14, 689-693
26. Cowart, M.; Faghih, R.; Curtis, M. P.; Gfesser, G. A.; Bennani, Y. L.; Black, L. A.; Pan, L.; Marsh, K. C.; Sullivan, J. P.; Esbenshade, T. A.; Fox, G. B.; Hancock, A. A. J. Med. Chem. 2005, 48, 38-55
27. Sun, M.; Zhao, C.; Gfesser, G. A.; Thiffault, C.; Miller, T. R.; Marsh, K.; Wetter, J.; Curtis, M.; Faghih, R.; Esbenshade, T. A.; Hancock, A. A.; Cowart, M. J. Med. Chem. 2005, 48, 6482-6490
28. Ando, K.; Kawamura, Y.; Akai, Y.; Kunitomo, J.-i.; Yokomizo, T.; Yamashita, M.; Shunsaku, O.; Ohishi, T.; Ohishi, Y. Org. Biomol. Chem. 2008, 6, 296-307
29. Verghese, J.; Liang, A.; Sidhu, P. P. S.; Hindle, M.; Zhou, Q.; Desai, U. R. Bioorg. Med. Chem. Lett. 2009, 19, 4126-4129
30. For other biological activities, see: Kawasaki, K.-i.; Masubuchi, M.; Morikami, K.; Sogabe, S.; Aoyama, T.; Ebiike, H.; Niizuma, S.; Hayase, M.; Fujii, T.; Sakata, K.; Shindoh, H.; Shiratori, Y.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. Lett. 2003, 13, 87-91
31. Buckley, G.; Cooper, N.; Dyke, H. J.; Galleway, F.; Gowers, L.; Gregory, J. C.; Hannah, D. R.; Haughan, A. F.; Hellewell, P. G.; Kendall, H. J.; Lowe, C.; Maxey, R.; Montana, J. G.; Naylor, R.; Picken, C. L.; Runcie, K. A.; Sabin, V.; Tuladhar, B. R.; Warneck, J. B. H. Bioorg. Med. Chem. Lett. 2000, 10, 2137-2140
32. Öztürk, S. E.; Akgül, Y.; An, H. Bioorg. Med. Chem. 2008, 16, 4431-4437
33. Haning, H.; Mueller, U.; Schmidt, G.; Schmeck, C.; Voehringer, V.; Kretschmer, A.; Bischoff, H. Bioorg. Med. Chem. Lett. 2007, 17, 3992-3996
34. Wyatt, P. G.; Allen, M. J.; Chilcott, J.; Foster, A.; Livermore, D. G.; Mordaunt, J. E.; Scicinski, J.; Woollard, P. M. Bioorg. Med. Chem. Lett. 2002, 12, 1399-1404
35. Pautus, S.; Yee, S. W.; Jayne, M.; Coogan, M. P.; Simons, C. Bioorg. Med. Chem. 2006, 14, 3643-3653
36. Bakunov, S. A.; Bakunova, S. M.; Wenzler, T.; Barszcz, T.; Werbovetz, K. A.; Brun, R.; Tidwell, R. R. J. Med. Chem. 2008, 51, 6927-6944
37. Chen, Y.; Chen, S.; Lu, X.; Cheng, H.; Ou, Y.; Cheng, H.; Zhou, G.-C. Bioorg. Med. Chem. Lett. 2009, 19, 1851-1854
38. Howlett, D. R.; Perry, A. E.; Godfrey, F.; Swatton, J. E.; Jennings, K. H.; Spitzfaden, C.; Wadsworth, H.; Wood, S. J.; Markwell, R. E. Biochem. J. 1999, 340, 283-289
39. Twyman, L. J.; Allsop, D. A Tetrahedron Lett. 1999, 40, 9383-9384
40. Rizzo, S.; Rivière, 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
41. Saitoh, M.; Kunitomo, J.; Kimura, E.; Iwashita, H.; Uno, Y.; Onishi, T.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C. D.; Dougan, D. R.; Textor, G. P.; Snell, G. P.; Takizawa, M.; Itoh, F.; Kori, M. J. Med. Chem. 2009, 52, 6270-6286
42. For a recent review on the synthesis of 2-substituted benzofurans, see: De Luca, L.; Nieddu, G.; Porcheddu, A.; Giacomelli, G. Curr. Med. Chem. 2009, 16, 1-20
43. For strategies on the synthesis of 2,3-disubstituted benzofurans, see: Katritzky, A. R.; Ji, Y.; Fang, Y.; Prakash, I. J. Org. Chem. 2001, 66, 5613-5615 and references cited therein.
44. For selected reviews on the synthesis of benzofurans by transition metal-catalyzed transformations, see: Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3160
45. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680
46. Cacchi, S.; Fabrizi, G.; Goggiamani, A. Curr. Org. Chem. 2006, 10, 1423-1455
47. Bates, C. G.; Saejueng, P.; Murphy, J. M.; Venkataraman, D. Org. Lett. 2002, 4727-4729
48. Eidamshaus, C.; Burch, J. D. Org. Lett. 2008, 10, 4211-4214
49. For electrophilic cyclization chemistry, see: Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296
50. Cho, C.-H.; Neuenswander, B.; Lushington, G.; Larock, R. C. J. Comb. Chem. 2008, 10, 941-947
51. Manarin, F.; Roehrs, J. A.; Mozzaquatro Gay, R.; Brandão, R.; Menezes, P. H.; Nogueira, C. W.; Zeni, G. J. Org. Chem. 2009, 74, 2153-2162
52. Prasada Rao Lingam, V. S.; Vinodkumar, R.; Mukkanti, K.; Thomas, A.; Gopalan, B. Tetrahedron Lett. 2008, 49, 4260-4264
53. Kanazawa, C.; Goto, K.; Terada, M. Chem. Commun. 2009, 5248-5250
54. Dyed cellulose and protein textiles, 1965, 5 pp: FR 1390842 19650219, CAN 63:89591, AN 1965:489591.
55. Wishka, D. G.; Walker, D. P.; Corbett, J. W.; Reitz, S. C.; Rauckhorst, M. R.; Groppi, V. E., Jr. PCT Int. Appl., 2003, 224 pp. CODEN: PIXXD2 WO 2003022856, A1 20030320, CAN 138:238006, AN 2003:221697.
56. Makovetskii, V. P.; Dzvinchuk, I. B.; Yaremko, V. V.; Svishchuk, A. A. Ukr. Khim. Zh. 1979, 45, 652-655
57. King, T. J.; Newall, C. E. J. Chem. Soc. 1965, 974-977
58. Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, 2361-2364
59. Demerseman, P.; Guillaumel, J.; Cheutin, A.; Royer, R. Bull. Soc. Chim. Fr. 1970, 2253-2261
60. Rao, M. L. N.; Awasthi, D. K.; Banerjee, D. Tetrahedron Lett. 2007, 48, 431-434 and references cited therein.
61. Deprets, S.; Kirsch, G. Eur. J. Org. Chem. 2000, 1353-1357
62. Einhorn, J. F.; Demerseman, P.; Royer, R. Synthesis 1984, 978-980
63. Lebel, H.; Leogane, O. Org. Lett. 2006, 8, 5717-5720
64. For a recent review on synthetic methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation, see: Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449
65. Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936
66. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940
67. Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944
68. Cundy, D. J.; Forsyth, S. A. Tetrahedron Lett. 1998, 39, 7979-7982
69. For a brief overview of the reactions of benzofuran-2-boronic acid, see: Petasis, N. A.; Goodman, A.; Zavialov, I. A. Tetrahedron 1997, 53, 16463-16470
70. Chen, C.; Wilcoxen, K.; Strack, N.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 827-830
71. Oh, C. H.; Jung, H. H.; Kim, K. S.; Kim, N. Angew. Chem., Int. Ed. 2003, 42, 805-808
72. Buszek, K. R.; Brown, N. Org. Lett. 2007, 9, 707-710
73. Wang, Z.; Elokdah, H.; McFarlane, G.; Pan, S.; Antane, M. Tetrahedron Lett. 2006, 47, 3365-3369
74. Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 4129-4131
75. Liu, Y.; Yan, W.; Chen, Y.; Petersen, J. L.; Shi, X. Org. Lett. 2008, 10, 5389-5392
76. Lan, J.-B.; Zhang, G.-L.; Yu, X.-Q.; You, J.-S.; Chen, L.; Yan, M.; Xie, R.-G. Synlett 2004, 1095-1097
77. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428
78. Altman, R. A.; Buchwald, S. L. Nat. Protoc. 2007, 2, 2474-2479
79. For a Cu-catalyzed N -arylation of an oxazolidinone derivative with 2-bromobenzofuran, see: Tatsumi, R.; Fujio, M.; Satoh, H.; Katayama, J.; Takanashi, S.-i.; Hashimoto, K.; Tanaka, H. J. Med. Chem. 2005, 48, 2678-2686
80. For the direct bromination of benzofuran, see: Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244-6251
81. Hussain, M.; Hung, N. T.; Langer, P. Tetrahedron Lett. 2009, 50, 3929-3932
82. Judd, D. B.; Dowle, M. D.; Middlemiss, D.; Scopes, D. I. C.; Ross, B. C.; Jack, T. I.; Pass, M.; Tranquillini, E.; Hobson, J. E.; Panchal, T. A.; Stuart, P. G.; Paton, J. M. S.; Hubbard, T.; Hildtich, A.; Drew, G. M.; Robertson, M. J.; Clark, K. L.; Travers, A.; Hunt, A. A. E.; Polley, J.; Eddershaw, P. J.; Bayliss, M. K.; Manchee, G., R.; Donnelly, M. D.; Walker, D. G.; Richards, S. A. J. Med. Chem. 1994, 37, 3108-3120
83. Klepacz, A.; Zwierzak, A. Tetrahedron Lett. 2001, 42, 4539-4540
84. Śliwińska, A.; Zwierzak, A. Tetrahedron 2003, 59, 5927-5934
85. Huang, H.-C.; Chamberlain, T. S.; Selbert, K.; Koboldt, C. M.; Isakson, P. C.; Reitz, D. B. Bioorg. Med. Chem. Lett. 1995, 20, 2377-2380
86. Dai, W.-M.; Lai, K. W. Tetrahedron Lett. 2002, 43, 9377-9380
87. Yamaguchi, T.; Irie, M. J. Org. Chem. 2005, 70, 10323-10328
88. For examples of Suzuki-Miyaura reactions with 3-bromobenzofuran derivatives, see refs 37, 51a, and 51b and also see: Nordvall, G.; Sundquist, S.; Johansson, G.; Glas, G.; Nilvebrant, L.; Hacksell, U. J. Med. Chem. 1996, 39, 3269-3277
89. Gfesser, G. A.; Faghih, R.; Bennani, Y. L.; Curtis, M. P.; Esbenshade, T. A.; Hancock, A. A.; Cowart, M. D. Bioorg. Med. Chem. Lett. 2005, 15, 2559-2563
90. Saitoh, M.; Kunitomo, J.; Kimura, E.; Hayase, Y.; Kobayashi, H.; Uchiyama, N.; Kawamoto, T.; Tanaka, T.; Mol, C. D.; Dougan, D. R.; Textor, G. S.; Snell, G. P.; Itoh, F. Bioorg. Med. Chem. 2009, 17, 2017-2029
91. James, C. A.; Coelho, A. L.; Gevaert, M.; Forgione, P.; Snieckus, V. J. Org. Chem. 2009, 74, 4094-4103
92. Militsopoulou, M.; Bariamis, S. E.; Athanassopoulos, C. M.; Papaioannou, D. Synthesis 2008, 3433-3442
93. For examples of Suzuki-Miyaura reactions with 3-iodobenzofuran derivatives, see: Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432-1434
94. Colobert, F.; Castanet, A.-S.; Abillard, O. Eur. J. Org. Chem. 2005, 3334-3341
95. For an "inverse-Suzuki" reaction involving the benzofuran-2-boronic acid, pinacol ester, prepared from the corresponding 2-bromobenzofuran, and aryl iodides, see: Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451-2454
96. For the protection of the free NH moiety of a 4-bromopyrrole-2- carboxylate to avoid extensive dehalogenation, see: Handy, S. T.; Bregman, H.; Lewis, J.; Zhang, X.; Zhang, Y. Tetrahedron Lett. 2003, 44, 427-430
97. For an example of a Suzuki reaction with a compound, namely tert -butyl-3-bromo-2-(4-(methylthio)phenyl)benzofuran-5-ylcarbamate, containing a free NH group that is not problematic, see ref 51b.
98. Nakasutka, S.; Asano, O.; Goto, T. Heterocycles 1986, 24, 2791-2792
99. Beyersbergen van Henegouwen, W. G.; Fieseler, R. M.; Rutjes, F. P. J. T.; Hiemstra, H. J. Org. Chem. 2000, 65, 8317-8325
100. Madin, A.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. Angew. Chem., Int. Ed. 2000, 39, 2934-2937
101. Carato, P.; Yous, S.; Sellier, D.; Poupaert, J. H.; Lebegue, N.; Berthelot, P. Tetrahedron 2004, 60, 10321-10324
102. Fukuyama, T.; Liu, G. J. Am. Chem. Soc. 1996, 118, 7426-7427
103. For the reductive dehalogenation in the course of Suzuki-Miyaura couplings, see: Handy, S. T.; Mayi, D. Tetrahedron Lett. 2007, 48, 8108-8110
104. Ghosez, L.; Franc, C.; Denonne, F.; Cuisinier, C.; Touillaux, R. Can. J. Chem. 2001, 79, 1827-1839
105. Cao, P.; Qu, J.; Burton, G.; Rivero, R. A. J. Org. Chem. 2008, 73, 7204-7208
106. Handy, S. T.; Wilson, T.; Muth, A. J. Org. Chem. 2007, 72, 8496-8500
107. Lythgoe, D. J.; McClenaghan, R. C. A. J. Heterocycl. Chem. 1993, 30, 113-117
108. For the chemoselective cleavage of Boc in the presence of Cbz, see: Nazih, A.; Heissler, D. Synthesis 2002, 203-206
109. For an overview of the chemistry of DMAP, see: Scriven, E. F. V. Chem. Soc. Rev. 1983, 12, 129-161
110. Hassner, A.; Krespi, L. R.; Alexanian, V. Tetrahedron 1978, 34, 2069-2076
111. Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569-583
112. Ragnarsson, U.; Grehn, L. Acc. Chem. Res. 1998, 31, 494-501
113. For the deprotecting agents and their use, see: Wuts, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis, 4rd ed.; John Wiley & Sons: New York, 2006.
114. To the best of our knowledge, hydrazine is the single amine known to be a nucleophilic deprotecting agent for the N -Cbz group, see: Chorev, M.; Klausner, Y. S. J. Chem. Soc., Chem. Commun. 1976, 596a
115. For the use of the fluoride anion as a nucleophilic agent for the deprotection of the N -Cbz group, see: Jacquemard, U.; Bénéteau, V.; Lefoix, M.; Routier, Mérour, J.-Y.; Coudert, G. Tetrahedron 2004, 60, 10039-10047