141089-99-8Relevant academic research and scientific papers
Influence of Phenylthio and Alkylthio Substituents on the Reactivity of 1-Oxa-1,3-butadienes in Hetero Diels-Alder Reactions
Tietze, Lutz F.,Fennen, Jens,Wichmann, Juergen
, p. 1507 - 1512 (2007/10/02)
The synthesis of the cyclic enamino ketones 1-3 bearing an alkylthio or an phenylthio group and their reactivity in hetero Diels-Alder reactions with enol ethers is described.Only compound 3 with an phenylthio group undergoes a cycloaddition with 16a-d to afford the diastereomeric adducts 17a-d and 18a-d.To estimate the activation by a phenylthio and alkylthio group semiempirical PM3/RHF calculations of the frontier orbital energies and coefficients of different enamine carbaldehydes have been performed.Key Words: Enamino ketones / 1,4-Thiazines / Hetero Diels-Alder reactions / Pyrans, dihydro / Calculations, semiempirical
