A novel and efficient 4-oxothiazolidine-1,2-dithiole rearrangement induced by Lawesson's reagent

Tetrahedron Letters

Volumn 44, Issue 37, 2003, Pages 7087-7090

  Markovic, Rade ^a,b   Baranac, Marija ^a,b   Jovetic, Stanka ^c  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSITY OF NOVI SAD   (Serbia)

Author keywords

Dithioles; Rearrangements; Thiazolidines

Indexed keywords

AMPHOLYTE; AROMATIC COMPOUND; REAGENT; THIAZOLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0042659138     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01721-0     Document Type: Article

References (16)

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10. A mechanism involving a concerted thiazolidine ring opening-closing process occurring simultaneously with hydrogen transfer is also conceivable.
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12. Crystallographic data (excluding structure factors) for this structure have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 208829. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
13. The formation of 4-mercaptothiazole 4d from β-enamino ester 1d involves an initial replacement of the C(4) oxygen by sulfur, inducing the spontaneous thione-thiol and enamino-imine tautomerizations resulting in unusual aromatization of the thiazolidine ring.
14. McKinnon D.M. Katritzky A.R., Rees C.W., Potts K.T. Comprehensive Heterocyclic Chemistry. 6:1981;783-811 Pergamon Press, Oxford.
15. The rather high chemical shift of the NH proton in 3c might also be explained by intramolecular hydrogen bonding between the ring nitrogen and NH proton; however, this requires an E-configurated double bond.
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