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Thefirst successful inverse electron-demand Diels–Alder has beendemonstrated with the 2-pyrone methyl coumalate in conjunctionwith substituted indoles. Utilizing 1-alkyl-3-chloroindoles as theelectron-rich dienophile efficiently generates carbazoles withoutthe need for additional metal catalysts. Through a thermal, one-potDiels–Alder/decarboxylation/eliminationdomino sequence, access to a class of 3-methylcarbazoles is rapidlygenerated with exclusive regiocontrol in up to 90% yield. [ABSTRACT FROM AUTHOR]

The process leads to formation of various substituted benzoates on reaction of title ester (II) with vinyl ethers, ketals or ortho esters as equivalents of vinyl ether dienophiles and extrusion of carbon dioxide. [ABSTRACT FROM AUTHOR]