SCOPUS 정보 검색 플랫폼

Volumn , Issue 24, 2007, Pages 3977-3980

Copper-catalyzed synthesis of 2,3-disubstituted indoles

Author keywords

BINOL; Copper catalyst; Domino reactions; Indoles; One pot synthesis

Indexed keywords

EID: 34548062130 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.200700428 Document Type: Article

Times cited : (64)

References (24)

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21
- 34548085060
- Experimental procedure for the synthesis of 3: A mixture of 2-iodoaniline (0.1 g, 0.46 mmol, ethyl acetoacetate (66 mg, 0.51 mmol, CuI (8.4 mg, 0.046 mmol, BINOL (17.5 mmol, 0.092 mmol) and Cs2CO 3 (0.15 g, 0.46 mmol) in DMSO (1 mL) was stirred at room temp, for 4 h under an atmosphere of nitrogen. The mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried with MgSO4 and concentrated in vacuo. The residue was purified by preparative TLC (hexane/EtOAc, 3:1) to provide indole 3 (74 mg, 79, as a solid. Rr, 0.30 (hexane/EtOAc, 3:1, M.p. 153.9°C (decomp, IR (NaCl, ν, 3016, 1687, 1453, 1208, 1091 cm-1. 1H NMR (400 MHz, CDCl3, δ, 2.72 (s, 3 H, 3.93 (s, 3 H, 7.16-7.30 (m, 3 H, 8.08 (d, J, 7.6 Hz, 1 H, 8.67 (br. s, 1 H) ppm. 13C NMR 100 MHz, CDCl3, δ, 14.2, 50.8
- + 189.0790; found 189.0726.

22
- 0001060227
- The β-keto esters used in the reaction were purchased from commercial sources (R = Et, iPr, tBu, Ph), or prepared from methyl acetoacetate by the alkylation of the dianion (R = allyl, prenyl, and geranyl, see: M. P. Moyer, P. L. Feldman, H. Rapoport, J. Org. Chem. 1985, 50, 5223-5230)
- The β-keto esters used in the reaction were purchased from commercial sources (R = Et, iPr, tBu, Ph), or prepared from methyl acetoacetate by the alkylation of the dianion (R = allyl, prenyl, and geranyl, see: M. P. Moyer, P. L. Feldman, H. Rapoport, J. Org. Chem. 1985, 50, 5223-5230)

23
- 15444362226
- and from the corresponding methyl ketone by carboethoxylation (R = 2-naphthyl, 2-furyl, 2-thienyl, and 2-pyridyl, see M. J. Alves, A. G. Fortes, A. Lemos, C. Martins, Synthesis 2005, 555-558).
- and from the corresponding methyl ketone by carboethoxylation (R = 2-naphthyl, 2-furyl, 2-thienyl, and 2-pyridyl, see M. J. Alves, A. G. Fortes, A. Lemos, C. Martins, Synthesis 2005, 555-558).

24
- 34548067330
- Selected data for new indole derivatives. 5c: 1H NMR (400 MHz, CDCl3, δ, 1.35 (s, 9 H, 3.72 (s, 3 H, 7.09 (dt, J, 1.2, 7.6 Hz, 1 H, 7.20 (dd, J, 1.2, 7.6 Hz, 1 H, 7.30 (dt, J, 1.5, 8.0 Hz, 1 H, 7.83 (d, J, 7.6 Hz, 1 H, 8.84 (br. s, 1 H) ppm. 13C NMR (100 MHz, CDCl3, δ, 27.5 (3 × CH3, 38.5, 52.5, 115.0, 125.0, 125.1, 125.7, 128.2, 129.1, 130.6, 136.8, 173.0 ppm. 5e: IR: ν, 3305, 2925, 1669, 1457, 1201, 1084, 749 cm-1, 1H NMR (400 MHz, CDCl3, δ, 1.55 (s, 3 H, 1.61 (s, 3 H, 2.42 (q, J, 7.3 Hz, 2 H, 3.18 (t, J, 7.3 Hz, 2 H, 3.93 (s, 3 H, 5.16-5.22 (m, 1 H, 7.16-7.25 (m, 2 H, 7.28-7.32 (m, 1 H, 8.10-8.14 (m, 1 H, 8.69 (s, 1 H) ppm. 13C NMR 100 MHz, CDCl3, δ, 17.6, 25.7, 27.5, 28.0, 50.7, 103.8, 110.6, 121.3, 121.6, 122.3, 122.9, 127.1, 133.5, 134.5, 148.2, 166.4 p
- + 258.1494; found 258.1438.

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