New Findings on the Hemetsberger-Knittel Reaction (Synthetic Studies on Indoles and Related Compounds. XLIII.

…, N KOTAKE, T TAKAHASHI, K TOYONARI…

Index: Murakami, Yasuoki; Watanabe, Toshiko; Suzuki, Hideharu; Kotake, Nobuyo; Takahashi, Tomoko; Toyonari, Kiyono; Ohno, Masami; Takase, Kyoko; Suzuki, Takayuki; Kondo, Kazuhiro Chemical and Pharmaceutical Bulletin, 1997 , vol. 45, # 11 p. 1739 - 1744

Full Text: HTML

Citation Number: 16

Abstract

In the Hemetsberger-Knittel reaction for indole synthesis, the intermediate ethyl 2-azido-3- hydroxy-3-aryl-propionate (4) was found to be formed in the reaction of arylaldehyde 1 with ethyl azidoacetate at a lower temperature (-30° C) as the main product, while only ethyl 2- azidocinnamate (2) is known to be formed at a higher temperature (0° C). It was also found that fluoride ion was effective for obtaining 4. Compound 4 was converted to 2 in good ...