The use of propane phosphonic acid anhydride (PPAA) in the synthesis of N-acyloxythiazole-2(3H)-thiones

Synlett

Volumn , Issue 3, 2000, Pages 371-373

  Hartung, Jens ^a   Schwarz, Michaela ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Carbon radical precursor; Propane phosphonic acid anhydride; Pyridinethione; Thiazolethione; Thiohydroxamic acid

Indexed keywords

CARBON; HYDROXAMIC ACID; PHOSPHONIC ACID DERIVATIVE; PROPANE; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; POLYMERIZATION; PURIFICATION; SYNTHESIS;

EID: 0034007302     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

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3. For reviews and a monograph see: Crich, D. Aldrichimica Acta 1987, 20, 35. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. Walter, W.; Schaumann, E. Synthesis 1971, 111. Giese, B. Radicals in Organic Synthesis: The Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
4. For reviews and a monograph see: Crich, D. Aldrichimica Acta 1987, 20, 35. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413. Walter, W.; Schaumann, E. Synthesis 1971, 111. Giese, B. Radicals in Organic Synthesis: The Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
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23. 11, ester- and epoxide formations: Kessler, H.; Kühn, M.; Löschner, T. Liebigs Ann. 1986, 1. Kende, A.S.; Delair, P.; Blass, B.E. Tetrahedron Lett. 1994, 35, 8123.
24. 11, ester- and epoxide formations: Kessler, H.; Kühn, M.; Löschner, T. Liebigs Ann. 1986, 1. Kende, A.S.; Delair, P.; Blass, B.E. Tetrahedron Lett. 1994, 35, 8123.
25. The reason for the superiority of DABCO in these reactions is according to our observations in part due to an easier and more efficient removal of base and base-derived products from reaction mixture.
26. 4) and concentrated at room temperature at 10 mbar to afford N-acyloxythiazolthiones as tan (2a, 2b, 4a, 4b, 7), orange (2c), or colorless solids (9), or as tan oil (8) The above given procedure was also applied for the synthesis of N-acyloxypyridinethiones 6.
27. 2 (231.3): calcd. C 45.27, H 2.85, N 6.60, S 30.31; found C 44.93, H 2.82, N 6.48, S 29.98.