Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: Facile synthesis of 2-benzoxepin-3(1H)- ones Dedicated to the memory of my teacher Professor P.V. Subba Rao, Department of Chemistry, Andhra University, Visakhapatnam

Tetrahedron

Volumn 69, Issue 47, 2013, Pages 10098-10107

  Reddy, A Gopi Krishna ^a   Krishna, J ^a   Satyanarayana, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY HYDERABAD   (India)

Author keywords

2 Benzoxepin 3(1H) ones; Condensation; Heck coupling; Oxy Michael addition; Pd catalysis; retro Oxy Michael addition

Indexed keywords

1 METHYL 2 BENZOXEPIN 3(1H) ONE; 2 BENZOXEPIN 3(1H) ONE; 6,7,8 TRIMETHOXY 2 BENZOXEPIN 3(1H) ONE; 7 (BENZYLOXY) 8 METHOXY 2 BENZOXEPIN 3(1H) ONE; 7,8 DIMETHOXY 1 METHYL 2 BENZOXEPIN 3(1H) ONE; 7,8 DIMETHOXY 2 BENZOXEPIN 3(1H) ONE; 8 (BENZYLOXY) 2 BENZOXEPIN 3(1H) ONE; 8 (BENZYLOXY) 7 METHOXY 2 BENZOXEPIN 3(1H) ONE; 8 METHOXY 1 METHYL 2 BENZOXEPIN 3(1H) ONE; 8 METHOXY 2 BENZOXEPIN 3(1H) ONE; 8,9 DIHYDRO[1,3]DIOXOLO[4,5 H][2]BENZOXEPIN 7(5H) ONE; [1,3]DIOXOLO[4,5 H][2]BENZOXEPIN 7(5H) ONE; ANALGESIC AGENT; BENZOXEPIN DERIVATIVE; ETHYL (5,6 DIMETHOXY 1,3 DIHYDRO 2 BENZOFURAN 1 YL)ACETATE; ETHYL 3 [2 [1 (3 ETHOXY 3 OXOPROPOXY)ETHYL] 4 METHOXYPHENYL]ACRYLATE; ETHYL 3 [6 [1 (3 ETHOXY 3 OXOPROPOXY)ETHYL] 1,3 BENZODIOXOL 5 YL]ACRYLATE; TERT BUTYL (5,6 DIMETHOXY 1,3 DIHYDRO 2 BENZOFURAN 1YL)ACETATE; TERT BUTYL 3 [2 (HYDROXYMETHYL) 4,5 DIMETHOXYPHENYL]ACRYLATE; TERT BUTYL 3 [2 [1 (3 TERT BUTOXY 3 OXOPROPOXY) ETHYL]PHENYL]ACRYLATE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ARTICLE; COVALENT BOND; CYCLIZATION; DRUG DEGRADATION; HECK REACTION; ISOMERIZATION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; RING OPENING; SOLVENT EFFECT; X RAY DIFFRACTION;

EID: 84886101868     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.09.050     Document Type: Article

References (101)

1. A. Ulaczyk-Lesanko, and D.G. Hall Curr. Opin. Chem. Biol. 9 2005 266 276
2. P.J. Parsons, C.S. Penkett, and A.J. Shell Chem. Rev. 96 1996 195 206
3. L.F. Tietze Chem. Rev. 96 1996 115 136
4. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945 2963
5. L.F. Tietze, H. Ila, and H.P. Bell Chem. Rev. 104 2004 3453 3516
6. A. Domling Chem. Rev. 106 2006 17 89
7. G. Zeni, and R.C. Larock Chem. Rev. 106 2006 4644 4680
8. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
9. B.B. Touré, and D.G. Hall Chem. Rev. 109 2009 4439 4486
10. J.L. Bras, and J. Muzart Chem. Rev. 111 2011 1170 1214
11. B. Liégault, J.-L. Renaud, and C. Bruneau Chem. Soc. Rev. 37 2008 290 299
12. R.V.A. Orru, and M. Greef Synthesis 10 2003 1471 1499
13. A. Bruggink, R. Schoevaart, and T. Kieboom Org. Process Res. Dev. 7 2003 622 640
14. S.P. Maddaford, N.G. Andersen, W.A. Cristofoli, and B.A. Keay J. Am. Chem. Soc. 118 1996 10766 10773
15. L.E. Overman, and M.D. Rosen Angew. Chem. 112 2000 4768 4771
16. Angew. Chem., Int. Ed. 39 2000 4596 4599
17. R. Grigg, P. Fretwell, C. Meerholtz, and V. Sridharan Tetrahedron 50 1994 359 370
18. M.R. Fielding, R. Grigg, V. Sridharan, M. Thornto-Pett, and C.J. Urch Tetrahedron 57 2001 7737 7748
19. L. Shi, C.K. Narula, K.T. Mak, L. Kao, Y. Xu, and R.F. Heck J. Org. Chem. 48 1983 3894 3900
20. G. Cuny, M. Bois-Choussy, and J. Zhu J. Am. Chem. Soc. 126 2004 14475 14484
21. H. Zhang, and R.C. Larock J. Org. Chem. 68 2003 5132 5138
22. A. Arcadi, S. Cacchi, G. Fabrizi, and F. Marinelli Synlett 2000 394 396
23. G. Dyker J. Org. Chem. 58 1993 6426 6428
24. X. Xu, Y. Qian, L. Yang, and W. Hu Chem. Commun. 2011 797 799
25. X. Xu, W.-H. Hu, P.Y. Zavalij, and M.P. Doyle Angew. Chem. 123 2011 11348 11351
26. Angew. Chem., Int. Ed. 50 2011 11152 11155
27. P. Peter Wipf, C.R.J. Stephenson, and K. Okumura J. Am. Chem. Soc. 125 2003 14694 14695
28. V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, and L. Balagopal Acc. Chem. Res. 36 2003 899 907
29. J. Zhu Eur. J. Org. Chem. 7 2003 1133 1144
30. W. Hu, X. Xu, J. Zhou, W.-J. Liu, H. Huang, J. Hu, L. Yang, and L.-Z. Gong J. Am. Chem. Soc. 130 2008 7782 7783
31. P. Truong, X. Xu, and M.P. Doyle Tetrahedron Lett. 52 2011 2093 2096
32. M. Shiri Chem. Rev. 112 2012 3508 3549
33. H. Lebel, C. Ladjel, and L. Brthous J. Am. Chem. Soc. 129 2007 13321 13326
34. M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, and M. Nomura J. Org. Chem. 63 1998 5211 5215
35. E.-I. Negishi, C. Copéret, S. Ma, S.-Y. Liou, and F. Liu Chem. Rev. 96 1996 365 393
36. C. Chowdhury, S. Mukherjee, B. Chakraborty, and B. Achari Org. Biomol. Chem. 9 2011 5856 5862
37. J. Lubkoll, A. Millemaggi, A. Perry, and R.J.K. Taylor Tetrahedron 66 2010 6606 6612
38. M.L.N. Rao, and P. Dasgupta Tetrahedron Lett. 53 2012 162 165
39. B. Laleu, and M. Lautens J. Org. Chem. 73 2008 9164 9167
40. N. Selander, and K.J. Szabó J. Org. Chem. 74 2009 5695 5698
41. Y. Cheng, Z. Duan, L. Yu, Z. Li, Y. Zhu, and Y. Wu Org. Lett. 10 2008 901 904
42. G. Satyanarayana, and M.E. Maier Org. Lett. 10 2008 2361 2364
43. I. Kim, and K. Kim Org. Lett. 12 2010 2500 2503
44. G. Satyanarayana, and M.E. Maier Eur. J. Org. Chem. 2008 5543 5552
45. O. Leogane, and H. Lebel Angew. Chem. 120 2008 356 358
46. Angew. Chem., Int. Ed. 47 2008 350 352
47. J. Barluenga, A. Mendoza, F. Rodríguez, and F.J. Fañanás Angew. Chem. 121 2009 1672 1675
48. Angew. Chem., Int. Ed. 48 2009 1644 1647
49. Y. Liang, T. Meng, H.-J. Zhang, and Z. Xi Synlett 2011 911 914
50. T. Toyoshima, Y. Mikano, T. Miura, and M. Murakami Org. Lett. 12 2010 4584 4587
51. A. Schweinitz, A. Chtchemelinine, and A. Orellana Org. Lett. 13 2011 232 235
52. F. Jafarpour, and N. Jalalimanesh Tetrahedron 68 2012 10286 10292
53. C.S. Cho, D.K. Lim, J.Q. Zhang, T.-J. Kim, and S.C. Shim Tetrahedron Lett. 45 2004 5653 5656
54. A.S.K. Hashmi, M. Ghanbari, M. Rudolph, and F. Rominger Chem. - Eur. J. 18 2012 8113 8119
55. A.S.K. Hashmi, C. Lothschütz, R. Döpp, M. Ackermann, J.D.B. Becker, M. Rudolph, C. Scholz, and F. Rominger Adv. Synth. Catal. 354 2012 133 137
56. A.S.K. Hashmi, C. Lothschütz, R. Döpp, M. Rudolph, T.D. Ramamurthi, and F. Rominger Angew. Chem. 121 2009 8392 8395
57. Angew. Chem., Int. Ed. 48 2009 8243 8246
58. R.-J. Song, Y. Liu, R.-J. Li, and J.-H. Li Tetrahedron Lett. 50 2009 3912 3916
59. L. Nassar-Hardy, S. Fabre, A.M. Amer, E. Fouquet, and F.-X. Felpin Tetrahedron Lett. 53 2012 338 341
60. Y. Zhou, Y. Zhao, X. Dai, J. Liu, L. Li, and H. Zhang Org. Biomol. Chem. 9 2011 4091 4097
61. J.-Y. Lee, and P. Ho Lee J. Org. Chem. 73 2008 7413 7416
62. T. Matsuda, M. Shigeno, and M. Murakami Org. Lett. 10 2008 5219 5221
63. Y. Zhao, Y. Zhou, L. Liang, X. Yang, F. Du, L. Li, and H. Zhang Org. Lett. 11 2009 555 558
64. J. Peng, D. Jiang, W. Lin, and Y. Chen Org. Biomol. Chem. 5 2007 1391 1396
65. E. Negishi, C. Copret, S. Ma, S.-Y. Liou, and F. Liu Chem. Rev. 96 1996 365 394
66. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
67. A.B. Dounay, and L.E. Overman Chem. Rev. 103 2003 2945 2964
68. J. Dupont, C.S. Consorti, and J. Spencer Chem. Rev. 105 2005 2527 2572
69. R.T. Ruck, M.A. Huffman, M.M. Kim, M. Shevlin, W.V. Kandur, and I.W. Davies Angew. Chem. 120 2008 4789 4792
70. Angew. Chem., Int. Ed. 47 2008 4711 4714
71. G. Satyanarayana, C. Maichle-Mössmerzb, and M.E. Maier Chem. Commun. 2009 1571 1573
72. Y. Hu, C. Yu, D. Ren, Q. Hu, L. Zhang, and D. Cheng Angew. Chem. 121 2009 5556 5559
73. Angew. Chem., Int. Ed. 48 2009 5448 5451
74. L.F. Tietze, A. Düfert, F. Lotz, L. Sölter, K. Oum, T. Lenzer, T. Beck, and R. Herbst-Irmer J. Am. Chem. Soc. 131 2009 17879 17884
75. O. René, D. Lapointe, and K. Fagnou Org. Lett. 11 2009 4560 4563
76. Z. Lu, C. Hu, J. Guo, J. Li, Y. Cui, and Y. Jia Org. Lett. 12 2010 480 483
77. M. Hussain, S.-M.T. Toguem, R. Ahmad, Crossed D sign.T. Tùng, I. Knepper, A. Villinger, and P. Langer Tetrahedron 67 2011 5304 5318
78. I. Ullah, M. Nawaz, A. Villinger, and P. Langer Tetrahedron Lett. 52 2011 1888 1890
79. Y. Terao, T. Satoh, M. Miura, and M. Nomura Tetrahedron 56 2000 1315 1320
80. S. Tua, Y. Shaa, L.-H. Xub, Z.-Y. Xiaoa, L.-Y. Yea, and J. Fanga J. Chem. Res. 2010 254 258
81. G. Dyker, and P. Grundt Tetrahedron Lett. 37 1996 619 622
82. M.W. Khan, and A.F.G.M. Reza Tetrahedron 61 2005 11204 11210
83. A. Rolfe, K. Young, and P.R. Hanson Eur. J. Org. Chem. 2008 5254 5262
84. L.D.L. Priebbenow, S.G. Stewartb, and F.M. Pfeffer Org. Biomol. Chem. 9 2011 1508 1515
85. D.L. Priebbenow, F.M. Pfeffer, and S.G. Stewart Eur. J. Org. Chem. 2011 1632 1635
86. A.G.K. Reddy, J. Krishna, and G. Satyanarayana Synlett 2011 1756 1760
87. J. Krishna, A.G.K. Reddy, L. Mahendar, and B.V. Ramulu Synlett 2012 375 380
88. L. Mahendar, J. Krishna, A.G.K. Reddy, and B.V. Ramulu Org. Lett. 14 2012 628 631
89. A.G.K. Reddy, and G. Satyanarayana Tetrahedron 68 2012 8003 8010
90. B. Suchand, J. Krishna, B.V. Ramulu, D. Dibyendu, A.G.K. Reddy, L. Mahendar, and G. Satyanarayana Tetrahedron Lett. 53 2012 3861 3864
91. A.G.K. Reddy, J. Krishna, and G. Satyanarayana Tetrahedron Lett. 53 2012 5635 5640
92. For xylarinol (A) and xylarinol (B), see: L. In-Kyoung, J. Yun-Woo, K. Young-Sook, Y.S. Hun, L.K. Jae, P. Seung-Moon, O. Byung-Taek, C. Jong-Chan, and Y.J. Bong-Sik Antibiotics 62 2009 163 165
93. For ulocladol, see: H. Ulrich, K. Gabriele, and D.W. Anthony Eur. J. Org. Chem. 11 1999 2949 2955
94. For alterlactone, see: A.H. Aly, R. Edrada-Ebel, I.D. Indriani, V. Wray, W.E.G. Müller, F. Totzke, U. Zirrgiebel, C. Schächtele, M.H.G. Kubbutat, W.H. Lin, P. Proksch, and R. Ebe J. Nat. Prod. 71 2008 972 980
95. A.A. Glukhov, N.F. Kirillov, A.A. Potapova, R.R. Makhmudov, and L.G. Mardanova Pharm. Chem. J. 44 2010 483 485
96. M. Yus, T. Soler, and F. Foubelo Tetrahedron 58 2002 7009 7016
97. C.H. Oh, and S.J. Park Tetrahedron Lett. 44 2003 3785 3787
98. T. Matsuda, M. Shigeno, and M. Murakami J. Am. Chem. Soc. 129 2007 12086 12087
99. C.S. Cho, and S.C. Shim Bull. Korean Chem. Soc. 27 2006 776 779 For review, see
100. J. Muzart Tetrahedron 61 2005 5955 6008
101. CCDC number for the compound 5ac CCDC 930424. Ministry of Science and Technology