Conversion of N,N'-bis(tert-butoxycarbonyl)guanidines to N-(N'-tert-butoxycarbonylamidino)ureas

Tetrahedron Letters

Volumn 39, Issue 12, 1998, Pages 1565-1568

  Miel, Hugues ^a   Rault, Sylvain ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE DERIVATIVE; UREA DERIVATIVE;

ARTICLE; SYNTHESIS;

EID: 0032546306     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00025-2     Document Type: Article

References (25)

1. 1.(a) Lammin, S.G.; Pedgrift, B.L. and Ratcliffe, A.J. Tetrahedron Lett. 1996, 37, 6815-6818
2. (b) Lal B. and Gangopadkyay, A.K. Tetrahedron Lett. 1996, 37, 2483-2486
3. (c) Bernatowicz, M.S.; Wu, Y. and Matsueda, G.R. Tetrahedron Lett. 1993, 37, 2483-86
4. (d) Drake, B.; Patel, M. and Lebl, M. Synthesis 1994, 579-582
5. (e) Iwanowicz, E.J.; Poss, M.A. and Lin J. Synth.Commun. 1993, 23, 1443-1445
6. (f) Poss, M.A.; Iwanowicz, E.J.; Reid, J.A.; Lin, J. and Gu, Z. Tetrahedron Lett. 1992, 33, 5933-5936
7. (g) Bergeron, J. and Mc Manis, J.S. J.Org.Chem. 1987, 52, 1700-1703.
8. 2.(a) Su, W. Synth.Commun. 1996, 26 (2), 407-413
9. (b) Chandrakumar, N.S. Synth.Commun. 1996, 26 (14), 2613-2616
10. (c) Kim, K.S. and Qian, L. Tetrahedron Lett. 1993, 34, 7677-7680.
11. 3.Yaw, F.W.; Kowalski, J.A.; Lipton, M.A. J. Org. Chem. 1997, 62, 1540-1542.
12. 4.For deprotection of bis-Cbz substituted guanidines, see ref. 2a and 2b. For deprotection of bis-Boc substituted guanidines, see Miel, H. and Rault, S. Tetrahedron Lett. 1997, 38, 7865-7866.
13. 5.Ko, S.Y.; Lerpiniere, J. and Christophi, M.A. Synlett 1995, 815-816.
14. 6.Chenguang, Y. and Williams, R.M. Tetrahedron Lett. 1996, 37, 1945-1948.
15. 7.Tilley, J.W. and Blount, J.F. Helv. Chem. Acta 1980, 63, 841-859.
16. 8.Tilley, J.W. and Blount, J.F. Helv. Chem. Acta 1980, 63, 832-840.
17. 9.The starting bis-Boc substituted guanidines are prepared from the corresponding amines according to reported procedures (see ref. 2a and 2b) by replacing bis-Cbz isothiourea with bis-Boc isothiourea.
18. 2, see ref. 14). (Equation presented) (b) Unexpected formation of 16 was realized by reacting diisopropylamine with N,N′-bis-Boc isothiourea. Despite the presence of the electrophilic central amidino carbon of isothiourea, no expected formation of bis-Boc isopropylguanidine was observed. (Equation presented) Drake and coll. (see ref. 1d) had also noted that reaction of diisopropylamine with another bis-Boc guanylating reagent (1-H-pyrazole-1-[N,N′-bis(tert-butoxycarbonyl)]carboxamidine) did not lead to the bis-Boc isopropylguanidine. The product they obtained was however not a pyrazole-Boc-carbamoyl carboxamidine resulting from the aminolysis of one Boc group but a diisopropylaminooxadiazinone.
19. 11.Bounkham, T. Synthesis 1997, 1189-1194 and references therein.
20. 12.(a) Kocienski, P.J. Protecting Groups; Thieme, New York 1994, 192-195
21. (b) Myers, A.G.; Yoon, T. Tetrahedron Lett. 1995, 36, 9429-9432.
22. 13.Lamothe, M.; Perez, M.; Colovray-Gotteland, V. and Halazy, S. Synlett 1996, 507-508.
23. 14.Levallet, C.; Lerpiniere, J. and Soo, Y.K. Tetrahedron 1997, 53, 5291-5304.
24. 15.Vaidyanathan, G. and Zalutsky, M.R. J. Org. Chem. 1997, 62, 4867-4869 see also Dharmpal, S.D. and Kozikowski, P.A. Tetrahedron Lett. 1994, 35, 977-980.
25. 15.Vaidyanathan, G. and Zalutsky, M.R. J. Org. Chem. 1997, 62, 4867-4869 see also Dharmpal, S.D. and Kozikowski, P.A. Tetrahedron Lett. 1994, 35, 977-980.