First inverse electron-demand Diels-Alder methodology of 3-chloroindoles and methyl coumalate to carbazoles.
The first successful inverse electron-demand Diels-Alder has been demonstrated with the 2-pyrone methyl coumalate in conjunction with substituted indoles. Utilizing 1-alkyl-3-chloroindoles as the electron-rich dienophile efficiently generates carbazoles without the need for additional metal catalysts. Through a thermal, one-pot Diels-Alder/decarboxylation/elimination domino sequence, access to a class of 3-methylcarbazoles is rapidly generated with exclusive regiocontrol in up to 90% yield.
Department of Chemistry and NSF Engineering Research Center for Biorenewable Chemicals, Iowa State University , Ames, Iowa 50011, United States.
Tezcan
T
Guney
Jennifer J
JJ
Lee
George A
GA
Kraus
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*
D002227:Carbazoles; D006843:Hydrocarbons, Chlorinated; D007211:Indoles; D011753:Pyrones