Synthesis and Conformational Analysis of the First 3-Oxa-7-thia-1- r-azabicyclo[3.3.0]-c-5-octane Single Functionalised at the C-5 Position

But, Andrada; Lameiras, Pédro; Silaghi‐Dumitrescu, Ioan; Batiu, Carmen; Guillard, Sophie; Ramondenc, Yvan; Darabantu, Mircea

doi:10.2174/157017810791130658

Cited by 3 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This residue was used without further purification. The 1 H NMR signals are in agreement with the reported spectroscopic data: 12 1 H NMR (DMSO-d 6 ) δ 2.70 (d, J = 9.0 Hz, 2 H), 2.86 (t, J = 9.0 Hz, 1 H SH ), 3.48 (d, J = 11.5 Hz, 2 H) 3.54 (d, J = 11.5 Hz, 2 H), 5.44 (bs, 2 H), 7.95 (s, 2 H).…”

Section: Methodssupporting

confidence: 90%

“…Our methodology for the synthesis of 6 provides a 40% overall yield in a two-step sequence; reported synthesis of Tris-SH was achieved in three steps with 48% overall . The authors only report the synthesis of bicycle 3 derived from formaldehyde, possibly indicating the limitation of the cyclization process starting from 6 .…”

Section: Resultsmentioning

confidence: 99%

“…12 The authors only report the synthesis of bicycle 3 derived from formaldehyde maybe indicating the limitation of the cyclization process starting from 6 .…”

Section: Resultsmentioning

confidence: 99%

“…Recently, Darabantu et al reported a synthesis of thiazolidinyloxazolidine 3 (R 1 = H), similarly starting from Tris 5 but otherwise using a different sequence . A more detailed discussion of these routes is provided below.…”

Section: Resultsmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and Ring-Chain-Ring Tautomerism of Bisoxazolidines, Thiazolidinyloxazolidines, and Spirothiazolidines

2011

View full text Add to dashboard Cite

The synthesis of fused heterocycles such as thiazolidinyl-oxazolidine 3 is described starting from Tris.HCl. The mercaptomethyl bisoxazolidine 8 was found to convert to the corresponding thiazolidinyloxazolidine 3 and the spiro-heterocycle 4 by a ring-chain-ring tautomerism, depending on the electronic nature of the ring substituents as well as the reaction conditions. This equilibration pathway is absent in the hydroxymethyl bisoxazolidines 2. Computational studies confirm that both kinetic and thermodynamic control features play a role in the product distribution.

show abstract

Section: Methodssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

“…12 The authors only report the synthesis of bicycle 3 derived from formaldehyde maybe indicating the limitation of the cyclization process starting from 6 .…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations