Efficient synthesis of 1,2,4-dithiazolidine-3,5-diones [dithiasuccinoyl- amines] from bis(chlorocarbonyl)disulfane plus bis(trimethylsilyl)amines

Journal of the American Chemical Society

Volumn 127, Issue 2, 2005, Pages 508-509

  Barany, Michael J ^a,c   Hammer, Robert P ^a,d   Merrifield, R B ^b   Barany, George ^a,b  

^a University of Minnesota   (United States)

^b ROCKEFELLER UNIVERSITY   (United States)

^c Roseville Area Schools   (United States)

^d LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 BIS(THIAZOLIDINE) 3,5 DIONE; AMINE; BIS(CHLOROCARBONYL)DISULFANE; BIS(TRIMETHYLSILYL)AMINE; CHLORINATED HYDROCARBON; HETEROCYCLIC AMINE; SILANE DERIVATIVE; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HYDROLYSIS; SYNTHESIS;

AMINES; SULFUR COMPOUNDS; THIAZOLIDINEDIONES; TRIMETHYLSILYL COMPOUNDS;

EID: 12944299300     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0455446     Document Type: Article

References (35)

1. The name dithiasuccinoyl-amine derives from the conceit that the heterocycle is the sulfurized analogue of a succinimide that represents a protected amine derivative. The present contribution introduces the first synthesis of Dts-amines that follows the intuitive notion that an analogue of succinyl chloride could be used to establish amino protection.
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26. Silylated amines can be acylated, in some cases more selectively and in higher yield than the corresponding free amines: (a) Birkofer, L.; Ritter, A. Angew. Chem., Int. Ed. Engl. 1965, 4, 417-429. (b) Klebe, J. F. Adv. Org. Chem. 1972, 8, 98-178. (c) Kricheldorf, H. R. Liebigs Ann. Chem. 1972, 763, 17-38. (d) Mironov, V. F.; Sheludyakov, V. D.; Kozyukov, V. P. Russ. Chem. Rev. 1979, 48, 473-489 (Engl. trans.).
27. Silylated amines can be acylated, in some cases more selectively and in higher yield than the corresponding free amines: (a) Birkofer, L.; Ritter, A. Angew. Chem., Int. Ed. Engl. 1965, 4, 417-429. (b) Klebe, J. F. Adv. Org. Chem. 1972, 8, 98-178. (c) Kricheldorf, H. R. Liebigs Ann. Chem. 1972, 763, 17-38. (d) Mironov, V. F.; Sheludyakov, V. D.; Kozyukov, V. P. Russ. Chem. Rev. 1979, 48, 473-489 (Engl. trans.).
28. Silylated amines can be acylated, in some cases more selectively and in higher yield than the corresponding free amines: (a) Birkofer, L.; Ritter, A. Angew. Chem., Int. Ed. Engl. 1965, 4, 417-429. (b) Klebe, J. F. Adv. Org. Chem. 1972, 8, 98-178. (c) Kricheldorf, H. R. Liebigs Ann. Chem. 1972, 763, 17-38. (d) Mironov, V. F.; Sheludyakov, V. D.; Kozyukov, V. P. Russ. Chem. Rev. 1979, 48, 473-489 (Engl. trans.).
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32. These results are not surprising, given the difficulty, discussed in refs 2 and 4g, in preparing 3 (R = H) by methods that suffice to elaborate 3 for most other substituents R. In the case under consideration, initial nitrogen/ silicon-containing products could be Tms-N=C=O [matches authentic standard] and/or TmsNH(C=0)Cl.
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