jo1c03072_si_001.pdf (7.6 MB)
Download fileInverse 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
journal contribution
posted on 2022-02-25, 15:04 authored by Li-Wen Shen, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Zhen-Hua Wang, Wei-Cheng YuanA 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 CS dienophiles, the developed protocol enables the formation
of diverse 3,6-dihydro-2H-1,3,4-thiadiazine derivatives
in excellent yields. In the presence of lithium aluminum hydride,
3,6-dihydro-2H-1,3,4-thiadiazine derivatives could
be further transformed into 5,6-dihydro-4H-1,3,4-thiadiazines
in good yields.