4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 6, Pages 4232-4240

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c03072

Keywords

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Funding

  1. National Natural Science Foundation of China [22171029, 21901024, 21871252, 21801024, 21801026]
  2. Sichuan Science and Technology Program [2021YFS0315]

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A highly selective reaction method using inverse electron demand was developed, allowing the formation of diverse compounds in high yields. The reaction involved the interaction between unsaturated thioesters and 1,2,1,3-diazadienes, generated in situ from alpha-halo hydrazones.
A highly regioselective inverse electron demand aza-Diels-Alder reaction of alpha,beta-unsaturated thioesters with 1,2-diaza-1,3-dienes generated in situ from alpha-halogeno hydrazones was developed. With alpha,beta-unsaturated thioesters as C=S 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.

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