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(c) Staschke, K. A.; Colacino, J. M.; Baxter, A. J.; Air, G. M.; Bansal, A.; Hornback, W. J.; Munroe, J. E.; Laver, W. G. Virology 1995, 214, 642-646.
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8
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There is little consensus in the literature over the use of the terms guanylation and guanidinylation. For a thorough discussion of guanidine terminology as used in the scientific community, see: Jones, J. H. J. Peptide Sci. 2002, 8, 285-287.
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0345266210
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note
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The term guanyl has officially been superseded by the term carbamimidoyl, and this conversion should technically be referred to as a carbamimidoylation; however, this is a rather laborious term and is rarely used in the literature.
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10
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0037012923
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For guanylations with reagent 2a, see: Hg promoted: (a) Yu, Y.; Ostresh, J. M.; Houghten, R. A. J. Org. Chem. 2002, 67, 3138- 3141.
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(b) Zhang, J.; Shi, Y.; Stein, P.; Atwal, K.; Li, C. Tetrahedron Lett. 2002, 43, 57-59.
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0035945998
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(c) Cunha, S.; Costa, M. B.; Napolitano, H. B.; Lariucci, C.; Vencato, I. Tetrahedron 2001, 57, 1671-1675.
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(e) Jirgensons, A.; Kums, I.; Kauss, V.; Kalvins, I. Synth. Comm. 1997, 27, 315-322.
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(h) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566-1568.
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(i) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936.
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Poss, M.A.1
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0037163267
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Other promoters: (j) Guisado, O.; Martínez, S.; Pastor, J. Tetrahedron Lett. 2002, 43, 7105-7109.
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0035847267
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For guanylations with reagent 2b, see: (a) Moroni, M.; Koksch, B.; Osipov, S. N.; Crucianelli, M.; Frigerio, M.; Bravo, P.; Burger, K. J. Org. Chem. 2001, 66, 130-133.
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(b) Guo, Z.-X.; Cammidge, A. N.; Horwell, D. C. Synth. Comm. 2000, 30, 2933-2943.
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0344403241
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Silver promoted: (g) Chen, B.-C.; Shiu, S.; Yang, D.-Y. J. Chin. Chem. Soc. 1998, 45, 549-553.
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For guanylations with reagent 2d, see: (a) Goodman, M.; Zapf, C.; Rew, Y. Biopolymers 2001, 60, 229-245.
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(b) Zapf, C. W.; Creighton. C. J.; Tomioka, M.; Goodman, M. Org. Lett. 2001, 3, 1133-1136.
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(c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038-1042.
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For guanylations with reagent 2e, see: (a) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161-2164.
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(c) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389-3392.
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0037131286
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For guanylations with other reagents, see: (a) Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. J. Org. Chem. 2002, 67, 7553-7556
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Hamilton, S.K.2
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Hamilton, G.S.J.4
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(c) Katritzky, A. R.; Rogovoy, B. V.; Chassaing, C.; Vvedensky, V. J. Org. Chem. 2000, 65, 8080-8082.
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(d) Isobe, T.; Fukuda, K.; Ishikawa, T. J. Org. Chem. 2000, 65, 7770-7773.
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(e) Isobe, T.; Fukuda, K.; Yamaguchi, K.; Seki, H.; Tokunaga, T.; Ishikawa, T. J. Org. Chem. 2000, 65, 7779-7785.
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43
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(f) Isobe, T.; Fukuda, K.; Tokunaga, T.; Seki, H.; Yamaguchi, K.; Ishikawa, T. J. Org. Chem. 2000, 65, 7774-7778.
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(g) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711-8714.
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45
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0034223083
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3 or pyrazole) with primary or secondary amines, although the yields for this type of reaction are generally low and require forcing conditions; see: (a) Pátek, M.; Smrcina, M.; Nakanishi, E.; Izawa, H. J. Comb. Chem. 2000, 2, 370-377.
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47
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0345266206
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note
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2). The terminology outlined in this paper avoids such confusions.
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48
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0344403242
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note
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3-X.
-
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49
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0345697804
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note
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This terminology is different from that proposed by Jones, who does not distinguish between the two reaction types and favors the use of guanidinylation to describe the conversion of an amine to a guanidine (see ref 5).
-
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-
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50
-
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0344403243
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note
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Unprotected guanidines, which are considerably more nucleophilic than their carbamate-protected counterparts, can be further functionalized under a variety of conditions, including conjugate addition, addition to aldehydes/ketones, and nucleophilic displacement. For some representative examples, see refs 18-20.
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51
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0033591151
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Conjugate additions: (a) Black, G. P.; Murphy, P. J.; Thornhill, A. J.; Walshe, N. D. A.; Zanetti, C. Tetrahedron 1999, 55, 6547-6554
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Black, G.P.1
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(b) Louwrier, S.; Tuynman, A.; Hiemstra, H. Tetrahedron 1996, 52, 2629-2646.
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Louwrier, S.1
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0037043491
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Addition of unprotected guanidines to aldehydes/ketones and nucleophilic displacements: (a) Nishikawa, T.; Urabe, D.; Yoshida, K.; Iwabuchi, T.; Asai, M.; Isobe, M. Org. Lett. 2002, 4, 2679-2682.
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Nishikawa, T.1
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Isobe, M.6
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(b) Nagasawa, K.; Georgieva, A.; Koshino, H.; Nakata, T.; Kita, T.; Hashimoto, Y. Org. Lett. 2002, 4, 177-180.
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Nagasawa, K.1
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(c) Franklin, A. S.; Gilbert, S. K. L.; Mackin, G. H.; Overman, L. E.; Shaka, A. J. J. Org. Chem. 1999, 64, 1512-1519.
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Franklin, A.S.1
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0035804953
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Other reactions of unprotected guanidines: (a) Overman, L. E.; Wolfe, J. P. J. Org. Chem. 2001, 66, 3167-3175.
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(c) Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 2000, 122, 4893-4903.
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67
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0345266184
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note
-
Characterization of compound 5k was problematic due to rotamers, and it was therefore deprotected to give 6k which was fully characterized.
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68
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0344403239
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219th National Meeting of the American Chemical Society, San Francisco CA, March 26-31, 2000; American Chemical Society: Washington, DC; MEDI-230
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Listed prices available from the Aldrich Chemical Co., 2002.
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0344834800
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