Recent advances and perspectives in the synthesis of heterocycles via carbenes

Tetrahedron

Volumn 71, Issue 16, 2015, Pages 2333-2347

  Krishnan, K Keerthi ^a   Thankachan, Amrutha P ^a   Anilkumar, Gopinathan ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

Carbenes; Heterocycles; Synthesis; Ylides

Indexed keywords

AZIRIDINE DERIVATIVE; CARBENOID; FURAN; HETEROCYCLIC COMPOUND; HETEROCYCLIC NITRO COMPOUND; NITROGEN; OXYGEN; PLATINUM; SCHIFF BASE; SULFUR; TETRAHYDROFURAN;

CHEMICAL REACTION; CYCLOADDITION; CYCLOPROPANATION; ORGANIC CHEMISTRY; PHOTOREACTIVITY; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; SYNTHESIS;

EID: 84925388096     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.02.061     Document Type: Review

References (126)

1. J. Clayden, N. Greeves, S. Warren, and P. Wothers Organic Chemistry 2001 University Press Oxford, New York, USA 1060 1061
2. P.S. Skell, and A.Y. Garner J. Am. Chem. Soc. 78 1956 5430 5433
3. W. Kirmse, and K. Kund J. Org. Chem. 55 1990 2325 2332
4. W.J. Baron, M.R. DeCamp, M.E. Hendrick, M. Jones Jr., R.H. Levin, and M.B. Sohn M. Jones Jr. R.A. Moss, Carbenes 1973 John Wiley & Sons New York, NY 1 17
5. H.M. Frey Adv. Photochem. 4 1966 225 256
6. D. Seyferth Acc. Chem. Res. 5 1972 65 74
7. G.M. Kaufman, J.A. Smith, G.G. Vander Stouw, and H. Schechter J. Am. Chem. Soc. 87 1965 935 937
8. W.M. Wagner Proc. Chem. Soc. 1959 229
9. C.M. Starks J. Am. Chem. Soc. 93 1971 195 199
10. M. Brookhart, and W.B. Staudabaker Chem. Rev. 87 1987 411 432
11. J.M. Walbrick, J.W. Wilson, and W.M. Jones J. Am. Chem. Soc. 90 1968 2895 2901
12. A. Padwa, and S.F. Hornbuckle Chem. Rev. 91 1991 263 309
13. H.S. Gill, and J.A. Landgrebe Tetrahedron Lett. 23 1982 5099 5102
14. H.S. Gill, and J.A. Landgrebe J. Org. Chem. 48 1983 1051 1055
15. E.Y. Kusei, M.S. Novikov, and A.F. Khlebnikov Russ. J. Org. Chem. 75 2005 1643 1647
16. S.J. Gharpure, M.K. Shukla, and U. Vijayasree Org. Lett. 11 2009 5466 5469
17. M. Dawid, D.L. Reid, J. Warkentin, and G. Mloston J. Phys. Org. Chem. 18 2006 86 89
18. Y. Cheng, and O. Meth-Cohn Chem. Rev. 104 2004 2507 2530
19. J. Barluenga, J. Santamaria, and M. Tomas Chem. Rev. 104 2004 2259 2283
20. F.C. da Silva, A.K. Jordao, D.R. da Rocha, S.B. Ferreira, A.C. Cunha, and V.F. Ferreira Curr. Org. Chem. 16 2012 224 251
21. D.M. Hodgson, A.H. Labande, and S. Muthusamy Org. React. 80 2013 133 496
22. O. Meth-Cohn Comprehensive Heterocyclic Chemistry 1984 Pergamon Oxford 665 668
23. A.W. Czarnik Acc. Chem. Res. 29 1996 112 113
24. H. Fischer, and K. Zeile Ann. Chem. 468 1929 98 116
25. D.C. Hodgkin, J. Pickworth, and J.H. Robertson Nature 176 1955 325 328
26. O.C. Dermer, and G.E. Hamm Ethylenimine and Other Aziridines 1969 Academic New York, NY 459 575
27. A. Stoll Helv. Chim. Acta 28 1945 1283 1308
28. R.V. Heinzelman, and J. Szmuszkovicz Prog. Drug Res. 6 1963 75 150
29. A.P. Gray, and D.E. Heitmeier J. Am. Chem. Soc. 81 1959 4347 4350
30. P. Rabe Chem. Ber. 41 1908 63 70
31. A.S. Konev, M.S. Novikov, and A.F. Khlebnikov Russ. J. Org. Chem. 43 2007 286 296
32. S. Oudeyer, E. Leonel, J.P. Paugam, and J.Y. Nedelec Tetrahedron 70 2014 919 923
33. M. Mihara, Y. Ishino, S. Minakata, and M. Komatsu J. Org. Chem. 70 2005 5320 5322
34. L.-Q. Cheng, and Y. Cheng Tetrahedron 63 2007 9359 9364
35. R.B. Morin, and M. Gorman Chemistry and Biology of β-lactam Antibiotics 1982 Academic New York, NY 315 360
36. T. Sperka, J. Pitlik, P. Bagossi, and J. Toezser Bioorg. Med. Chem. Lett. 15 2005 3086 3090
37. M.S. Novikov, A.F. Khlebnikov, M.V. Shevchenko, and D. Vidovic Russ. J. Org. Chem. 41 2005 1496 1506
38. M.S. Novikov, A.F. Khlebnikov, I.V. Voznyi, O.V. Besedina, and R.R. Kostikov Russ. J. Org. Chem. 41 2005 361 369
39. E.Y. Shinkevich, K.A. Tehrani, A.F. Khlebnikov, and M.S. Novikov Tetrahedron 64 2008 7524 7530
40. S.W. Kwok, L. Zhang, N.P. Grimster, and V.V. Fokin Angew. Chem., Int. Ed. 53 2014 3452 3456
41. S. Jansone-Popova, and J.A. May J. Am. Chem. Soc. 134 2012 17877 17880
42. Y. Shi, and V. Gevorgyan Org. Lett. 15 2013 5394 5396
43. D. Gauthier, R.H. Dodd, and P. Dauban Tetrahedron 65 2009 8542 8555
44. D.P. Chakraborty, and S. Roy Prog. Chem. Org. Nat. Prod. 57 1991 71 152
45. J. Yang, Q. Zhang, W. Zhang, and W. Yu Chem. Commun. 2014 13704 13707
46. X. Yangpeng, S. Guorong, W. Jing, L. Ping, and W. Yanguang Org. Lett. 16 2014 1244 1247
47. J. Diehl, and R. Bruckner Tetrahedron Lett. 55 2014 2629 2632
48. F. Miege, C. Meyer, and J. Cossy Org. Lett. 12 2010 4144 4147
49. B. Shi, W. Lewis, I.B. Campbell, and C.J. Moody Org. Lett. 11 2009 3686 3688
50. H. Neunhoeffer A.J. Boulton, Comprehensive Heterocyclic Chemistry II 6 1996 Pergamon Oxford, UK 507 573
51. A.H. Mark, P. Raffaele, L. William, and J.M. Christopher J. Org. Chem. 77 2012 1396 1405
52. P. Sharma, A. Kumar, and P. Pandey Ind. J. Chem. 45B 2006 2077 2082
53. M.S. Novikov, A.A. Amer, and A.F. Khlebnikov Tetrahedron Lett. 47 2006 639 642
54. R. Bonneau, and M.T.H. Liu Eur. J. Org. Chem. 2005 1532 1540
55. C.-X. Yan, Y. Zhao, X.-R. Wang, and Y. Cheng Tetrahedron 69 2013 10279 10283
56. J.H. Rigby, and P.J. Burke Heterocycles 67 2006 643 653
57. J.H. Rigby, and S. Sidique Org. Lett. 9 2007 1219 1221
58. U. Anthoni, C. Christophersen, and F.H. Nielsen S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives 13 1999 Wiley New York, NY 163 236
59. G. Regina, and J.S. Thomas Nat. Prod. Rep. 26 2009 1063 1094
60. F. Sondheimer Chem. Ber. 1 1965 454
61. V. Anupam, S.N. Pandeya, and S. Shweta Intl. J. Res. Ayurveda Pharm. 2 2011 1110 1116
62. A.D. Cross Q. Rev. 14 1960 317 335
63. V.K. Yadav, and V. Sriramurthy Angew. Chem., Int. Ed. 43 2004 2669 2671
64. B. Bajtos, M. Yu, H. Zhao, and B.L. Pagenkopf J. Am. Chem. Soc. 129 2007 9631 9634
65. Y. Sugita, C. Kimura, H. Hosoya, S. Yamadoi, and I. Yokoe Tetrahedron Lett. 42 2001 1095 1098
66. D.E. Fuerst, B.M. Stoltz, and J.L. Wood Org. Lett. 2 2000 3521 3523
67. R.B. Chhor, B. Nosse, S. Sorgel, C. Bohm, M. Seitz, and O. Reiser Chem. - Eur. J. 9 2003 260 270
68. G.K. Murphy, and F.G. West Org. Lett. 8 2006 4359 4361
69. M.J. Gonzalez, E. Lopez, and R. Vicente Chem. Commun. 2014 5379 5381
70. M. Liao, S. Dong, G. Deng, and J. Wang Tetrahedron Lett. 47 2006 4537 4540
71. R.K. Akhani, A.-U. Rehman, and W.F.K. Schnatter Tetrahedron Lett. 50 2009 930 932
72. P.A. Allegretti, and E.M. Ferreira Org. Lett. 13 2011 5924 5927
73. H. Cao, H. Zhan, J. Cen, J. Lin, Y. Lin, Q. Zhu, M. Fu, and H. Jiang Org. Lett. 15 2013 1080 1083
74. D. Verga, F. Doria, M. Mella, and M. Freccero J. Org. Chem. 74 2009 5311 5319
75. A. Caballero, M.M. Diaz-Requejo, S. Trofimenko, T.R. Belderrain, and P.J. Perez J. Org. Chem. 70 2005 6101 6104
76. P.A. Allegretti, and E.M. Ferreira J. Am. Chem. Soc. 135 2013 17266 17269
77. G. Sanjeevkumar, H. Hanumanagoud, and K.M. Basavaraja J. Chem. Pharm. Res. 2 2010 387 392
78. V. Nair, S. Mathai, S.C. Mathew, and N.P. Rath Tetrahedron 61 2005 2849 2856
79. V. Nair, A. Deepthi, M. Poonoth, B. Santhamma, S. Vellalath, B.P. Babu, R. Mohan, and E. Suresh J. Org. Chem. 71 2006 2313 2319
80. S. Muthusamy, and B. Ganaprakasam Tetrahedron 63 2007 3355 3362
81. W.C. Agosta, and S. Wolff J. Org. Chem. 40 1975 1027 1030
82. J. Adams, M. Poupart, L. Grenier, C. Schaller, N. Ouimet, and R. Frenette Tetrahedron Lett. 30 1989 1749 1752
83. Y. Cheng, Q. Zhu, Q.S. Li, and O. Meth-Cohn J. Org. Chem. 70 2005 4840 4846
84. M.D. Andrews, G.A. Brown, J.P.H. Charmant, T.M. Peakman, A. Rebello, K.E. Walsh, T. Gallagher, and N.J. Hales Chem. Commun. 1999 249 250
85. J.A. Zoltewicz, and L.V. Deady Adv. Heterocycl. Chem. 22 1978 71 121
86. J. Molina, O. Martins-filho, Z. Btener, D. Loebenberg, and A. Urbina Am. Soc. Microbiol. 44 2000 150 155
87. R.L. Borison, A.P. Patharaja, B.I. Diamond, and R.C. Maibach Psychopharmacol. Bull. 28 1992 213 218
88. K.A. Khistiaev, M.S. Novikov, A.F. Khlebnikov, and J. Magull Tetrahedron Lett. 49 2008 1237 1240
89. M.S. Novikov, A.F. Khlebnikov, K.A. Khistyaev, and I. Magull Russ. Chem. Bull. Int. Ed. 57 2008 1070 1079
90. U. Trstenjak, J. Ilas, and D. Kikelj Tetrahedron Lett. 54 2013 3341 3343
91. A.F. Khlebnikov, M.S. Novikov, P.P. Petrovskii, J. Magull, and A. Ringe Org. Lett. 11 2009 979 982
92. K. Nagarajan, J. David, R.S. Grewal, and T.R. Govindachari Ind. J. Exp. Biol. 12 1974 217 224
93. I.V. Voznyi, M.S. Novikov, A.F. Khlebnikov, and R.R. Kostikov Russ. J. Org. Chem. 42 2006 689 695
94. A. Padwa, S.M. Lynch, J.M. Mejia-Oneto, and H. Zhang J. Org. Chem. 70 2005 2206 2218
95. J.B. Summers, and B.P. Gunn J. Med. Chem. 43 2002 1082 1085
96. W.D. Shrader, W.B. Young, P.A. Sprengeler, J.C. Sangalang, K. Elrod, and G. Carr Bioorg. Med. Chem. Lett. 11 2001 1801 1804
97. M. Sanders Chem. Rev. 66 1966 297 339
98. G. Mloston, and H. Heimgartner Spec. Chem. Mag. 23 2003 38 40
99. W.S. Jenks, M.J. Heying, S.A. Stoffregen, and E.M. Rockafellow J. Org. Chem. 74 2009 2765 2770
100. J.P. John, and A.V. Novikov Org. Lett. 9 2007 61 63
101. B. Lu, Y. Li, Y. Wang, D.H. Aue, Y. Luo, and L. Zhang J. Am. Chem. Soc. 135 2013 8512 8524
102. M.I. Helen, Osborn, and J. Sweeney Tetrahedron: Asymmetry 8 1997 1693 1715
103. W. McCoull, and F.A. Davis Synthesis 10 2000 1347 1365
104. T. Hiyama Organofluorine Compounds 2000 Springer Berlin, Germany 272 280
105. M.V. Raimondi, S. Cascioferro, D. Schillaci, and S. Petruso Eur. J. Med. Chem. 41 2006 1439 1445
106. S. Higgins J. Chem. Soc. Rev. 26 1997 247 257
107. B.P.J. de Lacy Costello, P. Evans, N. Guernion, N.M. Ratcliffe, P.S. Sivanand, and G.C. Teare Synth. Met. 114 2000 181 188
108. G. Casiraghi, F. Zanardi, G. Rassu, and L. Pinna Org. Prep. Proced. Int. 28 1996 641 682
109. R.E. Nizurski-Mann, and M.P. Cava Heterocycles 34 1992 2003 2027
110. C. D'Silva, and D.A. Walker J. Org. Chem. 63 1998 6715 6718
111. C. Marti, and E.M. Carreira J. Am. Chem. Soc. 127 2005 11505 11515
112. J.M. Humphrey, Y. Liao, A. Ali, T. Rein, Y.-L. Wong, H.J. Chen, A.K. Courtney, and S.F. Martin J. Am. Chem. Soc. 124 2002 8584 8592
113. C. Bressv, C. Menant, and O. Piva Synlett 2005 577 582
114. X. Wu, G. Qui, K.K. Cheung, and K.F. Cheng Tetrahedron 53 1997 13323 13328
115. S. Hanessian, E. Balaux, D. Musil, L.L. Olsson, and I. Nilsson Bioorg. Med. Chem. Lett. 10 2000 243 247
116. S. Hanessian, and G. McNaughton-Smith Bioorg. Med. Chem. Lett. 6 1996 1567 1572
117. S. Madapa, Z. Tusi, and S. Batra Curr. Org. Chem. 12 2008 1116 1183
118. M.L. Bolognesi, R. Budriesi, A. Chiarini, E. Poggesi, A. Leonardi, and C. Melchiorre J. Med. Chem. 41 1998 4484 4853
119. X.L. Hou, H.Y. Cheung, T.Y. Hon, P.L. Kwan, T.H. Lo, S.Y. Tong, and H.N.C. Wong Tetrahedron 54 1998 1955 2020
120. W.J. Houlihan, M.L. Lee, P.G. Munder, G.M. Nemecek, D. Handley, C.M. Winslow, J. Happy, and C. Jaeggi Lipids 22 1987 884 890
121. G.A. Doherty, G.X. Yang, E. Borges, L.L. Chang, M. Maccoss, S. Tong, U. Kidambi, L.A. Egger, E. Mccauley, G.V. Riper, R.A. Mumford, J.A. Schmidt, and W.K. Hagmann Bioorg. Med. Chem. Lett. 12 2002 1501 1505
122. A. Khandelwal, R. Narayanan, and B. Gopalakrishnan Bioorg. Med. Chem. 11 2003 4235 4244
123. C.N. Hodge, P.Y.S. Lam, C.J. Eyerman, P.K. Jadhav, Y. Ru, C.H. Fernandez, G.V. De Lucca, C.H. Chang, R.F. Kaltenbach, E.R. Holler, F. Woerner, W.F. Daneker, J. Emmett, C. Calabrese, and P.E. Aldrich J. Am. Chem. Soc. 120 1998 4570 4581
124. C. Marti, and E.M. Carreira Eur. J. Org. Chem. 12 2003 2209 2219
125. M. Velusamy, K.R. Justin Thomas, J.T. Lin, Y.C. Hsu, and K.C. Ho Org. Lett. 7 2005 1899 1902
126. K.R. Justin Thomas, J.T. Lin, Y.C. Hsu, and K.C. Ho Chem. Commun. 2005 4098 4100