Synthetic Strategies for Preparing Bicyclic Guanidines

European Journal of Organic Chemistry

Volumn 2015, Issue 9, 2015, Pages 1869-1886

  Lemrová, Barbora ^a   Soural, Miroslav ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

Cycli zation; Guanidines; Nitrogen heterocycles; Solid phase synthesis

Indexed keywords

EID: 85027919971     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201403185     Document Type: Article

References (98)

1. Fu, X., Tan, C.H., Chem. Commun. 47 (2011), 8210–8222.
2. Coles, M.P., Chem. Commun. 25 (2009), 3659–3676.
3. Maji, B., Stephenson, D.S., Mayr, H., ChemCatChem 4 (2012), 993–999.
4. Nakata, K., Shiina, I., Org. Biomol. Chem. 9 (2011), 7092–7096.
5. Martinez-Mayorga, K., Medina-Franco, J.L., Giulianotti, M.A., Pinilla, C., Dooley, C.T., Appel, J.R., Houghten, R.A., Bioorg. Med. Chem. 16 (2008), 5932–5938.
6. Di Braccio, M., Grossi, G., Signorello, M.G., Leoncini, G., Cichero, E., Fossa, P., Alfei, S., Damonte, G., Eur. J. Med. Chem. 62 (2013), 564–578.
7. Venuti, M.C., Alvarez, R., Bruno, J.J., Strosberg, A.M., Gu, L., Chiang, H.S., Massey, I.J., Chu, N., Fried, J.H., J. Med. Chem. 31 (1988), 2145–2152.
8. Martin, M.W., Newcomb, J., Nunes, J.J., Boucher, C., Chai, L., Epstein, L.F., Faust, T., Flores, S., Gallant, P., Gore, A., Gu, Y., Hsieh, F., Huang, X., Kim, J.L., Middleton, S., Morgenstern, K., Oliveira-dos-Santos, A., Patel, V.F., Powers, D., Rose, P., Tudor, Y., Turci, S.M., Welcher, A.A., Zack, D., Zhao, H., Zhu, L., Zhu, X., Ghiron, C., Ermann, M., Johnston, D., Saluste, C.G.P., J. Med. Chem. 51 (2008), 1637–1648.
9. Dalla Via, L., Gia, O., Magno, S.M., Da Settimo, A., Marini, A.M., Farmaco 56 (2001), 159–167.
10. McKay, A.F., Hatton, W.G., Brown, R.O., J. Am. Chem. Soc. 78 (1956), 6144–6147.
11. McKay, A.F., Kreling, M.E., Can. J. Chem. 35 (1957), 1438–1445.
12. Hino, K., Irie, A., Uno, H., Chem. Pharm. Bull. 23 (1975), 1696–1701.
13. Shimada, J., Kuroda, T., Suzuki, F., J. Heterocycl. Chem. 30 (1993), 241–246.
14. Meszarosova, K., Holy, A., Masojidkova, M., Collect. Czech. Chem. Commun. 65 (2000), 1109–1125.
15. Janeba, Z., Holy, A., Masojidkova, M., Collect. Czech. Chem. Commun. 66 (2001), 517–532.
16. Belmont, P., Alarcon, K., Demeunynck, M., Lhomme, J., Bioorg. Med. Chem. Lett. 9 (1999), 233–236.
17. Matasi, J.J., Brumfield, S., Tulshian, D., Czarnecki, M., Greenlee, W., Garlisi, C.G., Qiu, H., Devito, K., Chen, S.C., Sun, Y., Bertorelli, R., Geiss, W., Le, V.D., Martin, G.S., Vellekoop, S.A., Haber, J., Allard, M.L., Bioorg. Med. Chem. Lett. 21 (2011), 3805–3808.
18. Ho, G.D., Silverman, L., Bercovici, A., Puchalski, C., Tulshian, D., Xia, Y., Czarniecki, M., Green, M., Cleven, R., Zhang, H., Fawzi, A., Bioorg. Med. Chem. Lett. 9 (1999), 7–12.
19. Gala, D., DiBenedetto, D.J., Kugelman, M., Mitchell, M.B., Tetrahedron Lett. 44 (2003), 2721–2723.
20. Gala, D., DiBenedetto, D., Gloor, G., Jenkins, J., Kugelman, M., Maloney, D., Miller, A., Org. Process Res. Dev. 8 (2004), 396–400.
21. Ren, S., Hesk, D., McNamara, P., Koharski, D., Hendershot, S., J. Labelled Compd. Radiopharm. 56 (2013), 480–484.
22. Verones, V., Flouquet, N., Farce, A., Carato, P., Leonce, S., Pfeiffer, B., Berthelot, P., Lebegue, N., Eur. J. Med. Chem. 45 (2010), 5678–5684.
23. Anisimova, V.A., Kuz'menko, V.V., Kuz'menko, T.A., Morkovnik, A.S., Russ. Chem. Bull. 56 (2007), 2315–2322.
24. Anisimova, V.A., Tolpygin, I.E., Russ. J. Org. Chem. 47 (2011), 1354–1361.
25. Anisimova, V.A., Tolpygin, I.E., Russ. J. Org. Chem. 47 (2011), 1346–1353.
26. Da Settimo, A., Da Settimo, F., Marini, A.M., Primofiore, G., Salerno, S., Viola, G., Dalla Via, L., Magno, S.M., Eur. J. Med. Chem. 33 (1998), 685–696.
27. Peet, N.P., Malecha, J., LeTourneau, M.E., Sunder, S., J. Heterocycl. Chem. 26 (1989), 257–264.
28. Friary, R., McPhail, A.T., Seidl, V., Collect. Czech. Chem. Commun. 58 (1993), 1133–1150.
29. Burbuliene, M.M., Bobrovas, O., Vainilavicius, P., J. Heterocycl. Chem. 43 (2006), 43–47.
30. Caldwell, J.P., Bennett, C.E., McCracken, T.M., Mazzola, R.D., Bara, T., Buevich, A., Burnett, D.A., Chu, I., Cohen-Williams, M., Josein, H., Hyde, L., Lee, J., McKittrick, B., Song, L., Terracina, G., Voigt, J., Zhang, L., Zhu, Z., Bioorg. Med. Chem. Lett. 20 (2010), 5380–5384.
31. Lipunova, G.N., Mokrushina, G.A., Granovskaya, E.B., Chasovskikh, O.M., Charushin, V.N., Mendeleev Commun., 1996, 15–17.
32. Kumar, R., Ermolatev, D.S., Van der Eycken, E.V., J. Org. Chem. 78 (2013), 5737–5743.
33. Bleda, J.A., Fresneda, P.M., Orenes, R., Molina, P., Eur. J. Org. Chem., 2009, 2490–2504.
34. Langer, P., Wuckelt, J., Doring, M., Schreiner, P.R., Gorls, H., Eur. J. Org. Chem., 2001, 2245–2255.
35. Ishikawa, F., Watanabe, Y., Chem. Pharm. Bull. 28 (1980), 1307–1310.
36. Pathak, R., Roy, A.K., Batra, S., Synlett, 2005, 848–850.
37. Frutos, R.P., Johnson, M., Tetrahedron Lett. 44 (2003), 6509–6511.
38. Frutos, R.P., Eriksson, M., Wang, X., Byrne, D., Varsolona, R., Johnson, M.D., Nummy, L., Krishnamurthy, D., Senanayake, C.H., Org. Process Res. Dev. 9 (2005), 137–140.
39. Wang, X., Zhang, L., Xu, Y., Krishnamurthy, D., Varsolona, R., Nummy, L., Shen, S., Frutos, R.P., Byrne, D., Chung, J.C., Farina, V., Senanayake, C.H., Tetrahedron Lett. 46 (2005), 273–276.
40. Temple, D.L., Yevich, J.P., Catt, J.D., Owens, D., Hanning, C., Covington, R.R., Seidehamel, R.J., Dungan, K.W., J. Med. Chem. 23 (1980), 1188–1198.
41. Esser, F., Pook, K.H., Carpy, A., Synthesis, 1990, 72–78.
42. Soukri, M., Guillaumet, G., Besson, T., Aziane, A., Aadil, M., Essassi, E.M., Akssira, M., Tetrahedron Lett. 41 (2000), 5857–5860.
43. Domon, L., Le Coeur, C., Grelard, A., Thiery, V., Besson, T., Tetrahedron Lett. 42 (2001), 6671–6674.
44. Elgazwy, S.H., Azab, M.E., Phosphorus Sulfur Silicon Relat. Elem. 173 (2001), 105–113.
45. Chowdhury, A.Z.M., Shibata, Y., Morita, M., Kaya, K., Hiratani, K., J. Heterocycl. Chem. 38 (2001), 1173–1177.
46. Magd El-Din, A., Elsharabasy, S., Hassan, A., Phosphorus Sulfur Silicon Relat. Elem. 181 (2006), 53–67.
47. Xu, T., Zhang, L., Xu, S., Yang, C.Y., Luo, J., Ding, F., Lu, X., Liu, Y., Tu, Z., Li, S., Pei, D., Cai, Q., Li, H., Ren, X., Wang, S.K., Angew. Chem. Int. Ed. 52 (2013), 8387–8390.
48. Khodair, A.I., Gesson, J.P., El-Ashry, E.S., Phosphorus Sulfur Silicon Relat. Elem. 179 (2004), 2653–2665.
49. Cox, D.A., Cross, P.E., J. Chem. Soc., 1970, 2134–2136.
50. Greenhill, J.V., Ismail, M.J., Edwards, P.N., Taylor, P.J., J. Chem. Soc. Perkin Trans. 2, 1985, 1255–1264.
51. Greenhill, J.V., Chaaban, I., Steel, P.J., J. Heterocycl. Chem. 29 (1992), 1375–1383.
52. Esser, F., Synthesis, 1987, 460–466.
53. Esser, F., Pook, K.H., Carpy, A., Leger, J.M., Synthesis, 1994, 77–82.
54. Watanabe, M., Okada, H., Teshima, T., Noguchi, M., Kakehi, A., Tetrahedron 52 (1996), 2827–2838.
55. Noguchi, M., Okada, H., Watanabe, M., Okuda, K., Nakamura, O., Tetrahedron 52 (1996), 6581–6590.
56. Okawa, T., Eguichi, S., Kakehi, A., J. Chem. Soc. Perkin Trans. 1, 1996, 247–254.
57. Okawa, T., Kawase, M., Eguchi, S., Kakehi, A., Shiro, M., J. Chem. Soc. Perkin Trans. 1, 1998, 2277–2286.
58. Bentya, A.V., Vaskevich, R.I., Turov, A.V., Rusanov, E.B., Vovk, M.V., Staninets, V.I., Russ. J. Org. Chem. 47 (2011), 1066–1073.
59. Ishikawa, F., Kosasayama, A., Nakamura, S., Konno, T., Chem. Pharm. Bull. 26 (1978), 3658–3665.
60. Ishikawa, F., Kosasayama, A., Konno, T., Chem. Pharm. Bull. 26 (1978), 3666–3674.
61. Romano, C., De la Cuesta, E., Avendano, C., Florencio, F., Sainz-Aparicio, J., Tetrahedron 44 (1988), 7185–7192.
62. Hassanabadi, A., Mosslemin, M.H., Anary-Abbasinejad, M., Koocheki, S., Monatsh. Chem. 144 (2013), 227–230.
63. Esser, F., Pook, K.H., Synthesis, 1992, 596–601.
64. Sakamoto, M., Miyazawa, K., Tomimatsu, Y., Chem. Pharm. Bull. 24 (1976), 2532–2540.
65. Lalezari, I., Sadeghi-Milani, S., J. Heterocycl. Chem. 16 (1979), 707–710.
66. Usachev, S., Gridnev, A., Synth. Commun. 41 (2011), 3683–3688.
67. Echavarren, A., Galan, A., De Mendoza, J., Salmeron, A., Lehn, J.M., Helv. Chim. Acta 71 (1988), 685–693.
68. Molina, P., Alajarin, M., Vidal, A., De la Concepcion Foces-Foces, M., Hernandez Cano, F., Tetrahedron 45 (1989), 4263–4286.
69. Molina, P., Alajarin, M., Vidal, A., J. Chem. Soc., Chem. Commun., 1992, 295–296.
70. Molina, P., Alajarin, M., Vidal, A., J. Org. Chem. 58 (1993), 1687–1695.
71. Molina, P., Lidon, M.J., Tarraga, A., Tetrahedron 50 (1994), 10029–10036.
72. Hirota, S., Sakai, T., Kitamura, N., Kubokawa, K., Kutsumura, N., Otani, T., Saito, T., Tetrahedron 66 (2010), 653–662.
73. Xie, C., Huang, N.Y., Ding, M.W., ARKIVOC (Gainesville, FL, U.S.), 2009, 220–232.
74. Zeng, F., Alper, H., Org. Lett. 12 (2010), 3642–3644.
75. Qiu, G., He, Y., Wu, J., Chem. Commun. 48 (2012), 3836–3838.
76. Shen, H., Wang, Y., Xie, Z., Org. Lett. 13 (2011), 4562–4565.
77. Wang, X., Jin, Y., Zhao, Y., Zhu, L., Fu, H., Org. Lett. 14 (2012), 452–455.
78. Xu, H., Fu, H., Chem. Eur. J. 18 (2012), 1180–1186.
79. Chen, D., Chen, Q., Liu, M., Dai, S., Huang, L., Yang, J., Bao, W., Tetrahedron 69 (2013), 6461–6467.
80. Ueda, T., Asahi, M., Nagai, S., Sakakibara, J., J. Heterocycl. Chem. 33 (1996), 169–172.
81. Ziegler, E., Steiger, W., Kappe, T., Monatsh. Chem. 99 (1968), 1499–1506.
82. Jen, T., Dienel, B., Bowman, H., Petta, J., Helt, A., Loev, B., J. Med. Chem. 15 (1972), 727–731.
83. Hardtmann, G.E., Heugi, B.S., Gogerty, J.H., Iorio, L.C., Barnes, H.W., J. Med. Chem. 14 (1971), 878–882.
84. Hardtmann, G.E., Koletar, G., Pfister, O.R., Gogerty, J.H., Iorio, L.C., J. Med. Chem. 18 (1975), 447–453.
85. Coppola, G.M., Hardtmann, G.E., Pfister, O.R., J. Org. Chem. 41 (1976), 825–831.
86. Coppola, G.M., Fraser, J.D., Hardtmann, G.E., Shapiro, M.J., J. Heterocycl. Chem. 22 (1985), 193–206.
87. Ruiz, M., Vasella, A., Helv. Chim. Acta 94 (2011), 785–800.
88. Ostresh, J.M., Schoner, C.C., Hamashin, V.T., Nefzi, A., Meyer, J.P., Houghten, R., J. Org. Chem. 63 (1998), 8622–8623.
89. Acharya, A.N., Nefzi, A., Ostresh, J.M., Houghten, R.A.R., J. Comb. Chem. 3 (2001), 189–195.
90. Kowalska, D., Liu, J., Appel, J.R., Ozawa, A., Nefzi, A., Mackin, R.B., Houghten, R.A., Mol. Pharmacol. 75 (2009), 617–625.
91. Lopez-Cremades, P., Molina, P., Aller, E., Lorenzo, A., Synlett, 2000, 1411–1414.
92. Kesarwani, A.P., Grover, R.K., Roy, R., Kundu, B., Tetrahedron 61 (2005), 629–635.
93. Hsiao, Y.S., Yellol, G.S., Chen, L.H., Sun, C.M., J. Comb. Chem. 12 (2010), 723–732.
94. Hsiao, Y.S., Narhe, B.D., Chang, Y.S., Sun, C.M., ACS Comb. Sci. 15 (2013), 551–555.
95. Chen, C.H., Yellol, G.S., Lin, P.T., Sun, C.M., Org. Lett. 13 (2011), 5120–5123.
96. Srivastava, G.K., Kesarwani, A.P., Grover, R.K., Roy, R., Srinivasan, T., Kundu, B., J. Comb. Chem. 5 (2003), 769–774.
97. McMaster, C., Fulopova, V., Popa, I., Grepl, M., Soural, M., ACS Comb. Sci. 16 (2014), 221–224.
98. Messina, I., Popa, I., Maier, V., Soural, M., ACS Comb. Sci. 16 (2014), 33–38.