A new synthesis of 4-oxygenated β-carboline derivatives by Fischer indolization

Tetrahedron Letters

Volumn 46, Issue 22, 2005, Pages 3831-3834

  Suzuki, Hideharu ^a   Tsukakoshi, Yoshiyuki ^a   Tachikawa, Takuya ^a   Miura, Yuusuke ^a   Adachi, Makoto ^a   Murakami, Yasuoki ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Acetalization; Aromatization; Fischer indolization; Indole; carboline

Indexed keywords

BENZENE DERIVATIVE; CARBOLINE DERIVATIVE;

ACETALIZATION; AROMATIZATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; FISCHER TROPSCH SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 18144409437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.177     Document Type: Article

References (41)

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35. 2-EtOAc (1:1) as a solvent system to afford the product (7) shown in Table 1
36. 2-EtOAc (1:1) as a solvent system to afford the product (8) shown in Table 2
37. 2-MeOH (10:1) as a solvent system to afford the product (10) shown in Table 3
38. One-pot procedure for 10a from 7a: To a stirred solution of compound (7a) (38.6 mg, 0.108 mmol) in 1,1,2,2-tetrachloroethane (2.0 mL), borontrifluoride etherate (0.36 mL, 2.9 mmol) was added at 0°C under argon atmosphere, and then the reaction mixture was heated to 120°C for 2 h. To the reaction mixture, dimethoxypropane (0.2 mL, 1.6 mmol) was added at 120°C, and heated at 120°C for 1 h. The reaction mixture was worked up as described above to afford the product (10a, 16.5 mg) in 77% yield
39. -1: 3345, 3255, 1595
40. -1: 3388, 1660
41. -1: 3447