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

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3601-3604

  Miyata, Okiko ^a   Kimura, Yasuo ^a   Muroya, Kanami ^a   Hiramatsu, Hajime ^b   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZINE DERIVATIVE; INDOLE;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HIGH TEMPERATURE; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0033617377     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00583-3     Document Type: Article

References (16)

1. 1. Reviews of Fischer indole synthesis: a) Robinson, B. Chem. Rev. 1963, 63, 373-401. b) Robinson, B.; Chem. Rev. 1969, 69, 227-250. c) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons, New York, 1982. d) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609-632.
2. 1. Reviews of Fischer indole synthesis: a) Robinson, B. Chem. Rev. 1963, 63, 373-401. b) Robinson, B.; Chem. Rev. 1969, 69, 227-250. c) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons, New York, 1982. d) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609-632.
3. 1. Reviews of Fischer indole synthesis: a) Robinson, B. Chem. Rev. 1963, 63, 373-401. b) Robinson, B.; Chem. Rev. 1969, 69, 227-250. c) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons, New York, 1982. d) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609-632.
4. 1. Reviews of Fischer indole synthesis: a) Robinson, B. Chem. Rev. 1963, 63, 373-401. b) Robinson, B.; Chem. Rev. 1969, 69, 227-250. c) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons, New York, 1982. d) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609-632.
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15. 1H-NMR spectrum with that of 5d.
16. 13. Energy levels (eV) of LUMO of several olefins shown below were calculated with a semiempirical MOPAC method utilizing a PM3 Hamiltonian and the CAChe system (SONY Tektronix). (equation presented)