Solid phase synthesis of guanidines

Tetrahedron

Volumn 53, Issue 19, 1997, Pages 6697-6705

  Robinson, Shaughnessy ^a   Roskamp, Eric J ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; GUANIDINE DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030948518     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00225-1     Document Type: Conference Paper

References (20)

1. Rathke, B. Chem. Ber., 1881, 14, 1774. Rathke, B. Chem. Ber., 1884, 17, 297.
2. Rathke, B. Chem. Ber., 1881, 14, 1774. Rathke, B. Chem. Ber., 1884, 17, 297.
3. Schow, S. "Cyanamide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 1408-1410.
4. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
5. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
6. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
7. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
8. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
9. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
10. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
11. Other reagents for the synthesis of guanidines include; Palmer, D. C. "S-Methylisothiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3523-3525. Cheon, S. H. "S-Methylisothiosemicarbazide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3522-3523. Campopiano, O. "Thiourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4885-4886. "Thiourea Dioxide" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4886-4888. Garratt, P. J. "Diphenyl Cyanocarbonimidate" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 2205-2207. Palmer, D. C. "O-Methylisourea" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 3525-3526. Bernatowicz, M. S. "1H-Pyrazole-1-carboxamidine Hydrochloride" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 4343-4344. Miller, A., Palmer, D. C. "Aminoiminomethanesulfonic Acid" Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed., Wiley, Sussex UK, 1996, Vol p 176-178.
12. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502. Tian, Z.; Roeske, R. W. Int. J. Peptide Protein Res. 1991, 37, 425-429.
13. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502. Tian, Z.; Roeske, R. W. Int. J. Peptide Protein Res. 1991, 37, 425-429.
14. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Syn. Commun. 1993, 23(10), 1443-1445. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34(48), 7677-7680. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z.Tetrahedron Lett. 1992, 33(40), 5933-5936. Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33(43), 6541-6542.
15. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Syn. Commun. 1993, 23(10), 1443-1445. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34(48), 7677-7680. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z.Tetrahedron Lett. 1992, 33(40), 5933-5936. Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33(43), 6541-6542.
16. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Syn. Commun. 1993, 23(10), 1443-1445. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34(48), 7677-7680. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z.Tetrahedron Lett. 1992, 33(40), 5933-5936. Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33(43), 6541-6542.
17. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Syn. Commun. 1993, 23(10), 1443-1445. Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34(48), 7677-7680. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z.Tetrahedron Lett. 1992, 33(40), 5933-5936. Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordani, C. Tetrahedron Lett. 1992, 33(43), 6541-6542.
18. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34(21), 3389-3392. Wu, Y.; Matsueda, G. R.; Bernatowicz, M. S. Synthetic Commun. 1993, 23(21), 3055-3060. Drake, B.; Patek, M. LeBel, M. Synthesis 1994, 6, 579-582.
19. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34(21), 3389-3392. Wu, Y.; Matsueda, G. R.; Bernatowicz, M. S. Synthetic Commun. 1993, 23(21), 3055-3060. Drake, B.; Patek, M. LeBel, M. Synthesis 1994, 6, 579-582.
20. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34(21), 3389-3392. Wu, Y.; Matsueda, G. R.; Bernatowicz, M. S. Synthetic Commun. 1993, 23(21), 3055-3060. Drake, B.; Patek, M. LeBel, M. Synthesis 1994, 6, 579-582.