Novel linker for the solid-phase synthesis of guanidines

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 5899-5902

  Josey, John A ^a   Tarlton, Catherine A ^a   Payne, Courtney E ^a  

^a AMGEN INC   (United States)

Author keywords

Combinatorial chemistry; Guanidines; Solid phase synthesis; Thioureas

Indexed keywords

GUANIDINE DERIVATIVE; RESIN; THIOUREA;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; PROTON TRANSPORT; SOLID STATE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032514431     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01242-8     Document Type: Article

References (18)

1. 1. For a review of solid-phase synthesis linkers see: Bunin, B. A. "The Combinatorial Index." San Diego: Academic Press, 1998:9-76.
2. 2. (a) Floyd, C. D.; Lewis, C. N.; Patel, S. R.; Whittaker, M, Tetrahedron Lett. 1996, 37, 8045-8048.
3. (b) Richter, L. S.; Desai, M. C. Tetrahedron Lett. 1997, 38, 321-322.
4. 3. Beaver, K. A.; Siegmund, A. C.; Spear, K. L. Tetrahedron Lett. 1996, 37, 1145-1148.
5. 4. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron Lett. 1997, 38, 7143-7146.
6. 5. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936.
7. 6. Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 623, 1540-1542.
8. 7. (a) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
9. (b) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711-8714 and references therein.
10. 8. Zhong, H. M.; Greco, M. N.; Maryanoff, B. E. J. Org. Chem. 1997, 62, 9326-9330.
11. 9. Drewry, D. H.; Gerritz, S. W.; Linn, J. A. Tetrahedron Lett. 1997, 38, 3377-3380.
12. 10. Hauske, J. R.; Dorff, P. Tetrahedron Lett. 1995, 36, 1589-1592.
13. 11. For an alternative see: Hernandez, A. S.; Hodges, J. C. J. Org. Chem. 1997, 62, 3153-3157.
14. 12. Higher percentage TFA resulted in decomposition of guanidines derived from secondary amines as evidenced by the presence of the secondary amine in HPLC, ES MS and NMR.
15. 4 has recently been reported. See: Miel, H.; Rault, S. Tetrahedron Lett. 1997, 38, 7865-7866.
16. 13C NMR, and positive ion ES MS consistent with the desired product.
17. 15. Atwal, K. S.; Ahmed, S. Z.; O'Reilly, B. C. Tetrahedron Lett. 1989, 30, 7313-7316.
18. 16. Overman, L. E.; Okazaki, M. E.; Mishra, P. Tetrahedron Lett. 1986, 27, 4391-4394.