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Letters in Organic Chemistry
Volumn 2, Issue 8, 2005, Pages 707-711
Preparation of azepinoindole derivatives via oxidative palladium couplings
Author keywords

Indole; Oxidant; Oxidative cyclisation; Palladium
Indexed keywords

EID: 36849070241     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017805774717490     Document Type: Review
Times cited : (7)
References (15)
  • 7
    • 46149097343 scopus 로고    scopus 로고
    • 2 (0.03 mmol) and benzoquinone (0.33 mmol) were added to a solution of 1 (0.33 mmol) in anhydrous THF/DMF (2:1, 6 mL). The final solution was heated at 80°C for 40 min. The reaction mixture was cooled and the solvents were distilled off. The crude residue was purified by column chromatography on silica gel to give 2.
    • 2 (0.03 mmol) and benzoquinone (0.33 mmol) were added to a solution of 1 (0.33 mmol) in anhydrous THF/DMF (2:1, 6 mL). The final solution was heated at 80°C for 40 min. The reaction mixture was cooled and the solvents were distilled off. The crude residue was purified by column chromatography on silica gel to give 2.
  • 8
    • 46149103832 scopus 로고    scopus 로고
    • Derivatives 1 were prepared by coupling reaction (EDCI, DMAP) between indole-2-carboxylic acid or 1-methylindole-2-carboxylic acid and 3-butenamine or N-substituted-3-butenamine (N-benzyl-3-butenamine, N-(4-methoxybenzyl, 3-butenamine, N-methyl-3-butenamine, Selected data for 1c and 1f. 1c: white solid; mp 137-138°C (EtOAc-petroleum ether, IR (KBr) v 3150, 1630 cm-1; 1H NMR (300 MHz, DMSO-d6) δ 2.92-2.99 (m, 2H, CH2, 4.12 (broad s, 2H, CH2, 5.44-5.60 (m, 4H, CH2, CH2, 6.25-6.39 (m, 1H, CH, 7.22 (broad s, 1H, HAr, 7.49 (t, 1H, J=7.5 Hz, HAr, 7.67 (t, 1H, J=8.3 Hz, HAr, 7.74-7.85 (m, 5H, HAr, 8.00 (d, 2H, J=8.3 Hz, HAr, 11.20 (broad s, 1H, NH, MS (EI) m/z 304 (M, HRMS (EI) for C20H20N2O, Calcd: 304.1576. Found: 304.1577. 1f. oil; IR
    • 2O, Calcd: 318.1732. Found: 318.1732.
  • 10
    • 46149116953 scopus 로고    scopus 로고
    • Selected data for 2c, 2d, 2f and 2g.2c: white solid; mp 162-164°C (EtOH, IR (KBr) v 3210, 1600 cm-1, 1H NMR (300 MHz, CDCl3) δ 2.42 (s, 3H, CH3, 3.65 (d, 2H, J=7.1 Hz, CH2, 4.86 (s, 2H, CH2, 5.64 (broad t, 1H, J=7.1 Hz, CH, 7.17 (t, 1H, J=7.9 Hz, HAr, 7.29-7.37 (m, 6H, HAr, 7.46 (d, 1H, J=8.3 Hz, HAr, 7.89 (d, 1H, J=8.1 Hz, HAr, 9.67 (broad s, 1H, NH, 13C NMR (75 MHz, CDCl3) δ 22.1 (CH3, 45.6 (CH2, 51.3 (CH2, 112.7 (CH, 118.8 (CH, 119.3 (C, 120.4 (CH, 122.5 (CH, 124.7 (CH, 125.7 (C, 127.6 (C, 128.1 (2 CH, 128.8 (2 CH, 130.7 (C, 136.7 (C, 137.3 (C, 137.7 (C, 163.3 (CO, MS (EI) m/z 302 (M, HRMS (EI) for C20H18 N2O, Calcd: 302.1419. Found: 302.1417. 2d: white solid; mp 166-168°C (EtOH, IR K
    • 2O Calcd: 240.1263. Found: 240. 1263.
  • 11
    • 46149125869 scopus 로고    scopus 로고
    • Allylations of 2-(2-aminophenyl)-1-methyl, 1-benzyl- or 1-phenylsulfonylindoles were performed in the presence of BuLi and allyl bromide to give N-allyl derivatives (eg 3a, N-Protection (alkylation or acylation) of these latter afforded compounds 3b, 3d and 3e. Compound 3c was prepared by final desulfonylation. Selected data for 3c and 3d. 3c: white solid; mp 142-143°C (washing Et2O, IR (KBr) v 3295, 1635 cm-1; 1H NMR (300 MHz, CDCl3) δ 1.87 (s, 3H, CH3, 3.64 (dd, 1H, J=7.6, 14.5 Hz, CH2, 4.76 (dd, 1H, J=5.7, 14.5 Hz, CH2, 5.03-5.13 (m, 2H, CH2, 5.83-5.98 (m, 1H, CH, 6.75 (d, 1H, J=1.3 Hz, HAr, 7.13 (t, 1H, J=7.4 Hz, HAr, 7.19-7.26 (m, 2H, HAr, 7.33-7.48 (m, 3H, HAr, 7.64 (d, 1H, J=79 Hz, HAr, 7.76 (dd, 1H, J=1.3, 7.7 Hz, HAr, 8.42 broad s, 1H, NH, MS
    • 2O, Calcd: 304.1576. Found: 304.1577.
  • 12
    • 46149099752 scopus 로고    scopus 로고
    • Selected data for 4c and 4d1 H and 13C NMR spectra of 4c and 4d indicate signals arising from rotamers. 4c; white solid; mp 182-183°C (dec, EtOAc, IR (KBr) v 1731, 1663 cm-1; 1H NMR (300 MHz, DMSO-d6) δ 1.32 (s, 9H, 3 CH3, 1.85 (s, 2.25H, CH3, 2.06 (s, 0.75H, CH3, 2.32 (d, 3H, J=1.1 Hz, CH3, 6.46 (d, 0.75H, J=1.1 Hz, CH, 6.56 (d, 0.25H, J=1.1 Hz, CH, 7.29-7.59 (m, 6H, HAr, 7.94 (d, 1H, J=7.9 Hz, HAr, 8.13 (d, 0.25H, J=8.3 Hz, HAr, 8.19 (d, 0.75H, J=8.3 Hz, HAr, 13C NMR (75 MHz, CDCl3) major rotamer is only described δ 18.7 (CH3, 22.1 (CH3, 27.8 (3 CH3, 84.2 (C, 114.9 (CH, 121.7 (CH, 122.1 (C, 123.3 (CH, 125.6 (CH, 126.7 (2 CH, 127.5 (CH, C, 128.2 (C, 129.1 (CH, 130.4 (CH, 131.0 (C, 135.1 (C, 137.8 C, 1
    • 2O, Calcd: 302.1419. Found: 302.1419.
  • 14
    • 46149121206 scopus 로고    scopus 로고
    • Selected data for 5a, 5b and 5c. 5a: white solid; mp 164-166°C (EtOAc-PE, IR (KBr) v 3220, 1595 cm-1; 1H NMR (300 MHz, CDCl3) δ 2.18-2.39 (m, 2H, CH2, 3.41-3.51 (m, 3H, 2 CH2, 3.64-3.73 (m, 1H, CH, 3.81 (s, 3H, CH3, 4.11 (dd, 1H, J=3.2, 11.1 Hz, CH2, 4.75 (d, 1H, J=14.5 Hz, CH2, 4.85 (d, 1H, J=14.5 Hz, CH2, 6.88 (d, 2H, J=8.7 Hz, HAr, 7.16 (t, 1H, J=7.2 Hz, HAr, 7.26-7.34 (m, 3H, HAr, 7.43 (d, 1H, J=8.3 Hz, HAr, 7.64 (d, 1H, J=8.1 Hz, HAr, 9.51 (s, 1H, NH, 13C NMR (75 MHz, CDCl3) δ 29.9 (CH2, 38.1 (CH, 44.3 (CH2, 48.1 (CH2, 51.8 (CH2, 55.4 (CH3, 112.5 (CH, 114.2 (2 CH, 116.8 (C, 120.1 (CH, 120.2 (CH, 124.9 (CH, 127.1 (C, 127.9 (C, 129.2 (C, 129.5 (2 CH, 129.8 C, 1
    • 2O, Calcd: 276.1029. Found:276.1030.
  • 15
    • 46149124956 scopus 로고    scopus 로고
    • Selected data for 6b and 6c.6b: white solid; mp > 210°C (EtOH, IR (KBr) v 3185, 1631 cm-1; 1H NMR (300 MHz, CDCl3) δ 1.87 (s, 3H, CH3, 3.22 (dd, 1H, J=11.3, 13.6 Hz, CH2, 3.84 (dd, 1H, J=7.2, 11.3 Hz, CH2, 4.07 (dd, 1H, J=2.6, 11.3 Hz, CH2, 4.39-4.49 (m, 1H, CH, 5.04 (dd, 1H, J=7.2, 13.6 Hz, CH2, 7.17 (t, 1H, J=7.5 Hz, HAr, 7.24-7.48 (m, 5H, HAr, 7.60 (d, 1H, J=7.9 Hz, HAr, 7.73 (d, 1H, J=7.9 Hz, HAr, 8.18 (broad s, 1H, NH, 13C NMR (75 MHz, DMS)-d6) δ 22.2 (CH3, 36.9 (CH, 47.1 (CH2, 50.7 (CH2, 111.6 (CH, 111.8 (C, 119.0 (CH, 119.2 (CH, 122.5 (CH, 1273 (CH, 127.6 (CH, 127.7 (C, 127.9 (2 CH, 129.1 (C, 131.2 (C, 136.7 (C, 141.8 (C, 168.2 (CO, MS (EI) m/z 324 (M, HRMS (EI) for C19
    • 2O, Calcd: 338.1186. Found:338.1184.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.