First Inverse Electron-Demand Diels–Alder Methodology of 3-Chloroindoles and Methyl Coumalate to Carbazoles

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• 作者：Tezcan Guney ; Jennifer J. Lee ; George A. Kraus
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：February 21, 2014
• 年：2014
• 卷：16
• 期：4
• 页码：1124-1127
• 全文大小：282K
• ISSN：1523-7052

文摘

The first successful inverse electron-demand Diels鈥揂lder 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鈥揂lder/decarboxylation/elimination domino sequence, access to a class of 3-methylcarbazoles is rapidly generated with exclusive regiocontrol in up to 90% yield.