Tetrahedron p. 1915 - 1924 (1988)
Update date:2022-08-02
Topics:
Dieter, Karl R.
Balke, Wiliam H.
Fishpaugh, Jeffrey R.
4-Ethyl-5-methyl-6-methylthio-2(H)-pyranone (4) undergoes Diel-Alder reactions with ethyl hexynoate (5), 3-heptyn-2-one (6), ethyl propiolate (7), and 3-butyn-2-one (8) to afford substitutes benzenes with high regioselectivity upon extrusion of CO2. 4-Ethyl-5,6-dimethyl- (1), 4-ethyl-3,6-dimethyl- (2) and 4-ethyl-5-methyl-(2H)-pyranone (3) gave excellent to good regioselectivity with internal alkynes 5 and 6 and poor regioselectivity with terminal alkynes 7 and 8.MNDO calculations have been carried out on the pyrones and alkynes and qualitative FMO analysis correctly predicts the major products.
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Doi:10.1016/0022-328X(88)80509-6
(1988)Doi:10.1007/s00706-008-0024-3
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(2020)Doi:10.1016/S0040-4039(00)82086-9
(1988)Doi:10.1016/j.tet.2016.08.069
(2016)
