In Situ Reagents For Thionation of Amides, Peptides and Lactams

References

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