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

1997; Pharmaceutical Society of Japan; Volume: 45; Issue: 11 Linguagem: Inglês

10.1248/cpb.45.1739

1347-5223

Yasuoki Murakami, Toshiko Watanabe, Hideharu Suzuki, Nobuyo KOTAKE, Tomoko Takahashi, Kiyono TOYONARI, Masami OHNO, K. TAKASE, Takayuki Suzuki, Kazuhiro Kondo,

Synthesis and Reactions of Organic Compounds

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 yield by treatment with SOCl2/pyridine or SOCl2/Et3N. A trial application of this reaction to ketone is also described.