Thermal cyclization of N-trifluoracetyl enehydrazines under mild conditions: A novel entry into the Fischer indole synthesis

Okiko Miyata, Yasuo Kimura, Kanami Muroya, Hajime Hiramatsu and Takeaki Naito*

*Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan, Email: taknaitokobepharma-u.ac.jp

O. Miyata, Y. Kimura, K. Muroya, H. Hiramatsu, T. Naito, Tetrahedron Lett., 1999, 40, 3601-3604.

DOI: 10.1016/S0040-4039(99)00583-3

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Abstract

An efficient thermal cyclization of N-trifluoroacetyl enehydrazines for the synthesis of indoles is described. Neither an elevated temperature (180-250°C) nor an acid catalyst is needed.

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Efficient Synthesis of Benzofurans Utilizing [3,3]-Sigmatropic Rearrangement Triggered by N-Trifluoroacetylation of Oxime Ethers: Short Synthesis of Natural 2-Arylbenzofurans

N. Takeda, O. Miyata, T. Naito, Eur. J. Org. Chem., 2007, 1491-1509.

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Key Words

Fischer Indole Synthesis, Indoles

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ID: J72-Y1999-170