First Inverse Electron-Demand Diels–Alder Methodology of 3-Chloroindoles and Methyl Coumalate to Carbazoles
T Guney, JJ Lee, GA Kraus
Index: Guney, Tezcan; Lee, Jennifer J.; Kraus, George A. Organic Letters, 2014 , vol. 16, # 4 p. 1124 - 1127
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Citation Number: 19
Abstract
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 ...
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