In situ Reagents For Thionation Of Amides, Peptides And Lactams

Synthetic Communications

Volumn 20, Issue 19, 1990, Pages 3085-3095

  Brillon, Denis ^a  

^a INRS INSTITUT ARMAND FRAPPIER   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000964734     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397919008051529     Document Type: Article

References (14)

1. (1) Preparation of difunctionalized enamines from thioamides: (a) Brillon, D.; Sauve, G., J. Org. Chem., 1990, 55, 2246–2249. (b) Sauve, G.; Le Berre, N.; Zacharie, B., Tetrahedron Lett., 1988, 29, 2299–2302.
2. (2) Preparation of 8b and of backbone-modified peptides from thiopeptides: Sauve, G.; Rao, V.S.; Lajoie, G. ; Belleau, B., Can. J. Chem., 1985, 63., 3089–3101.
3. (3) (a) Review: Cava, M.P.; Levinson, M.I., Tetrahedron, 1985, 41, 5061–5087. (b) Distillation instead of chromatography in the preparation of 17b: Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.O., Org. Synth., 1984, 62, 158–164.
4. (4) Preparation of 3b, 4b, 6b and thiopeptides: Lajoie, G.; Lepine, F.; Maziak, L.; Belleau, B., Tetrahedron Lett., 1983, 24. 3815—3818.
5. (5) Campaigne, E. Chem. Rev., 1946, 1, 39.
6. (6) Dash, B.; Dora, E.K.; Panda, C.S., Heterocycles, 1982, 19, 2093–2098.
7. (7) Goel, O.P.; Krolls, U., Synthesis, 1987, 162–164.
8. (8) Scheeren, J.W.; Ohms, P.H.J.; Nivard, R.J.F., Synthesis, 1973, 149–151.
9. (9) Hydrosulfuration-thionation of unsaturated amides: Alper, H.; Currie, J.K.; Sachdeva, R., Angew. Chem. Int. Ed. Engl., 1978, 17, 689–690.
10. (10) Reaction of P4S10 with NaHCO3 or n-BuLi7 involves phosphorus-sulfide bond breaking and formation of ionic thiophosphate groups.
11. (11) Reagents 1A and IB slowly transform7,8 due to solid particles or upon heating, to non reactive gelatinous mass. Filtration of the solution is better if heating of 1A or use of the less stable IB is considered. Preparation of IB on large scale is highly risky.
12. (12) Compound 15b (85%) was also prepared using Belleau's reagent4 (3 eq ; 30 h at 40°C).
13. (13) Thionation of acridones with P4S10 in HMPT at 110°C: Claude, S.; Lehn, J.M.; Vigneron, J.P., Tetrahedron Lett., 1989, 30, 941–944.
14. (14) 2 equivalents of NaOH (2M in water) can be used.