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Inverse Electron-Demand Aza-Diels-Alder Reaction of α,β-Unsaturated Thioesters with In Situ-Generated 1,2-Diaza-1,3-dienes for the Synthesis of 1,3,4-Thiadiazines.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2022 Mar 18; Vol. 87 (6), pp. 4232-4240. Date of Electronic Publication: 2022 Feb 25. - Publication Year :
- 2022
-
Abstract
- A highly regioselective inverse electron-demand aza-Diels-Alder reaction of α,β -unsaturated thioesters with 1,2-diaza-1,3-dienes generated in situ from α-halogeno hydrazones was developed. With α,β-unsaturated thioesters as C═S dienophiles, the developed protocol enables the formation of diverse 3,6-dihydro-2 H -1,3,4-thiadiazine derivatives in excellent yields. In the presence of lithium aluminum hydride, 3,6-dihydro-2 H -1,3,4-thiadiazine derivatives could be further transformed into 5,6-dihydro-4 H -1,3,4-thiadiazines in good yields.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 87
- Issue :
- 6
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 35212520
- Full Text :
- https://doi.org/10.1021/acs.joc.1c03072