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1. (a) Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1998, 54, 15385-15443;
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Hermkens, P.H.H.1
Ottenheijm, H.C.J.2
Rees, D.3
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5
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0022270704
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2. (a) Impromidine - Histamine H2 receptor agonist: Durant, G. J.; Ganellin, C. R.; Hills, D. W.; Miles, P. D.; Parsons, M. E.; Pepper, E. S.; White, G. R. J. Med. Chem. 1985, 28, 1414-1422;
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Durant, G.J.1
Ganellin, C.R.2
Hills, D.W.3
Miles, P.D.4
Parsons, M.E.5
Pepper, E.S.6
White, G.R.7
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6
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0029981644
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(b) Hypotensive - Caracasanamide: Corelli, F.; Dei, D.; Monoche, G. D.; Botta, B.; Delucca, C.; Carmiganni, M.; Volpe, A. R.; Botta, M. Biorg. Med. Chem. Lett. 1996, 6, 653-658;
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(1996)
Biorg. Med. Chem. Lett.
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Corelli, F.1
Dei, D.2
Monoche, G.D.3
Botta, B.4
Delucca, C.5
Carmiganni, M.6
Volpe, A.R.7
Botta, M.8
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7
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0028284740
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(c) Insulin Secretagogue - Potassium/ATP channel openner - BTS 67,582: Ohnota, H.; Koizumi, T.; Tsutsumi, N.; Kobayashi, M.; Inoue, S.; Sato, F. J. Pharmcol. Exp. Ther. 1994, 269, 489;
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Ohnota, H.1
Koizumi, T.2
Tsutsumi, N.3
Kobayashi, M.4
Inoue, S.5
Sato, F.6
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10
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0000911184
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(b) Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540-1542;
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Yong, Y.F.1
Kowalski, J.A.2
Lipton, M.A.3
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12
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0032506678
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(d) Schneider, S. E.; Bishop, P. A.; Salazar, M. A.; Bishop, O. A.; Anslyn, E. V. Tetrahedron 1998, 54, 15063-15086.
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Schneider, S.E.1
Bishop, P.A.2
Salazar, M.A.3
Bishop, O.A.4
Anslyn, E.V.5
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0013559857
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4. (a) Drewry, D. H.; Gerritz, S. W.; Linn, J. A. Tetrahedron Lett. 1997, 38, 337-3380;
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Drewry, D.H.1
Gerritz, S.W.2
Linn, J.A.3
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0032580389
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(c) Kearney, P. C.; Fernandez, M.: Flygare, J. A. Tetrahedron Lett. 1998, 39, 2663-2666;
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Kearney, P.C.1
Fernandez, M.2
Flygare, J.A.3
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17
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0030598080
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5. There are three methods which attach intact guanidines onto the solid support, but are considered beyond the scope of methodology developments such as this and those found in 3 and 4. These are: (a) Bonnat, M.; Bradley, M.; Kilburn, J. D. Tetrahedron Lett. 1996, 37, 5409-5412;
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(1996)
Tetrahedron Lett.
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Bonnat, M.1
Bradley, M.2
Kilburn, J.D.3
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18
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0030599243
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(b) Ref. 11 in Virgilio, A. A.; Schurer, S. C.; Ellman, J. A. Tetrahedron Lett. 1996, 37, 6961-6964;
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(1996)
Tetrahedron Lett.
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Virgilio, A.A.1
Schurer, S.C.2
Ellman, J.A.3
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19
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0001566714
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(c) Zhong, H. M.; Greco, M. N.; Marynoff, B. E. J. Org. Chem. 1997, 62, 9326-9330;
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(1997)
J. Org. Chem.
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Zhong, H.M.1
Greco, M.N.2
Marynoff, B.E.3
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0032516263
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(d) Nizi, E.; Botta, M.; Corelli, F.; Manetti, F.; Messina, F.; Maga, G. Tetrahedron Lett. 1998, 39, 3307-3310.
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(1998)
Tetrahedron Lett.
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Nizi, E.1
Botta, M.2
Corelli, F.3
Manetti, F.4
Messina, F.5
Maga, G.6
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6. This method utilizes alcohols and primary amines, and requires removal of excess reagent upon product release from the resin. Dodd, D. S.; Wallace, O. B. Tetrahedron Lett. 1998, 39, 5701-5704.
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(1998)
Tetrahedron Lett.
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Dodd, D.S.1
Wallace, O.B.2
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7. This method utilizes thioureas and amines. Josey, J. A.; Tarlton, C. A.; Payne, C. E. Tetrahedron Lett. 1998, 39, 5899-5902.
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(1998)
Tetrahedron Lett.
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Josey, J.A.1
Tarlton, C.A.2
Payne, C.E.3
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9. Similar solution phase guanidine chemistries: (a) Atwal, K. S.; Ahmed, S. Z.; O'Reilly, B. C. Tetrahedron Lett. 1989, 30, 7313-7316;
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(1989)
Tetrahedron Lett.
, vol.30
, pp. 7313-7316
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Atwal, K.S.1
Ahmed, S.Z.2
O'Reilly, B.C.3
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(b) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936;
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(1992)
Tetrahedron Lett.
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Poss, M.A.1
Iwanowicz, E.2
Reid, J.A.3
Lin, J.4
Gu, Z.5
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(d) Levallet, C.; Lerpiniere, J.; Ko, S. Y. Tetrahedron 1997, 53, 5291-5304;
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Levallet, C.1
Lerpiniere, J.2
Ko, S.Y.3
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(e) Barvian, M. R.; Showalter, H. D. H.; Doherty, A. M. Tetrahedron Lett. 1997, 38, 6799-6802.
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(1997)
Tetrahedron Lett.
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Barvian, M.R.1
Showalter, H.D.H.2
Doherty, A.M.3
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10. (a) Lorsbach, B. A.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717;
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(1996)
J. Org. Chem.
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Lorsbach, B.A.1
Miller, R.B.2
Kurth, M.J.3
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0013485341
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note
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-1): 3040, 2930, 1970 (N=C=S), 1700 (C=O), 1600, 1500, 1450, 1250, 1170, 1070, 1030, 910.
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32
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0013519262
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note
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12. These compounds were identical by HPLC and TLC with authentic samples which were purchased from their corresponding vendors: (a) entry 1 - Sigma #I9890; (b) entry 6 - ICN #158938; (c) entry 7 - Aldrich #D20,775-6.
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33
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0013559858
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note
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19F NMR, MS, and HPLC spectra.
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