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, 117 mg, 1.0 eq) was added to a solution of aqueous formaldehyde (1 mmol, 82 mg, 37 %, 2.0 eq) and allylamine (0.5 mmol, 57 mg, 1.0 eq) in 3 ml toluene. The stirred mixture was heated to reflux under Ar for 12 h. After completion of present reaction, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel
, 400 MHz, CDCl 3 ) ? 8.16 (d, J = 9.4 Hz, 2H, H-b), vol.7
C-a), 133.4 (C-5), 133.0(q, J = 35 Hz, C-2), 125.6 (C-b), 120.6(q, J = 271 Hz, C-1), 101 MHz, CDCl 3 ) ? 149.7 (C-d), vol.141, pp.56-63 ,
, , pp.1022-1023, 1068.
, 199 mg) was dissolved in 2.5mL cyclohexanone and the stirred mixture was heated to 130 o C under Ar for 12 h. After completion of present reaction, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography on silica gel
, 400 MHz, CDCl 3 )? 7.40-7.36 (m, 2H, H-b), 7.32-7.22 (m, 5H
, 101 MHz, CDCl 3 ) ? 143.0 (C-d), 140.8 (C-e), vol.133, pp.131-137
, , pp.1002-1003, 1015.
, mmol, 90 mg, 100 mol%) in acetonitrile (1.5 ml) was added methyl acrylate (2.5 mmol, 215 mg, 5 eq) and DBU(38 mg, 50 mol%), the mixture was stirred for 3 h at r.t. under Ar. After evaporation of solvent under reduced pressure, the residue crude (412 mg) was purified by column chromatography on silica gel
, 400 MHz, CDCl 3 ) ? 7.19-7.05 (m, 3H, H-a,c,d), 6.88 (d, J = 7.5 Hz, 1H, H-b), vol.6
CDCl 3 ) ? 172.4 (C-8), MHz, vol.137, issue.101 ,
, 127.6 (C-b), vol.126, pp.122-127
, HRMS: calculated for C 19 H 23 NO 6 : 361.1525, not found, fragment
, , vol.3001, pp.1179-1180, 1202.
, 4-dihydronaphthalen-1-yl)-4-nitroheptanedioate (0.5 mmol, 181 mg, 100 mol%) in DMF (1.5 ml) was added Cs 2 CO 3 (0.5 mmol, 163 mg
OAc) 2 (5 mol%), and dppe (5 mol%), the mixture was stirred for 30 min at 120 o C under ,
After evaporation of solvent under reduced pressure (vacuum, 80 o C), the residue crude (384 mg) was purified by column chromatography on silica gel ,
, 400 MHz, CDCl 3 ) ? 8.09 (d, J = 8.2 Hz, 1H, H-h), 7.89-7.82 (m, 1H, H-d), 7.73 (d, J = 8.1 Hz, vol.1
CDCl 3 ) ?173.8 (C-4), MHz, vol.139, issue.101 ,
, , vol.3001, pp.1014-1015, 1174.
, 4-dihydronaphthalen-1-yl)-5-nitropentan-2-one (IV-2d)
, mmol, 90 mg, 100 mol%) in acetonitrile (1.5 ml) was added but-3-en-2-one (1.5 mmol, 105 mg, 3 eq) and DBU(15 mg, p.10
, After evaporation of solvent under reduced pressure, the residue crude (229 mg) was purified by column chromatography on silica gel, the mixture was stirred for 3 h at r.t. under Ar
CDCl 3 ) ? 206.7 (C-8), 136.2 (C-2), MHz, vol.132, issue.101 ,
, 127.8 (C-b), vol.128, pp.122-123
, HRMS: calculated for C 15 H 17 NO 3 :259.1208, found 259, p.1201
, , pp.1023-1024, 1167.
, To a solution of 4-(nitromethyl)-1,2-dihydronaphthalene (0.5 mmol, 90 mg, 100 mol%
, Pd(OAc) 2 (5 mol%), and dppe (5 mol%), the mixture was stirred for 30 min at 120 o C under Ar. After evaporation of solvent under reduced pressure (vacuum, 80 o C), the residue crude (297 mg) was purified by column chromatography on silica gel, DMF (1.5 ml) was added Cs 2 CO 3 (0.5 mmol, 163 mg, 100 mol%)
, 400 MHz, CDCl 3 ) ? 8.04 (d, J = 8.1 Hz, 1H, H-d), 7.89 (d, J = 7.4 Hz, vol.1
, MHz, vol.134, issue.101
, C-h), 125.8 (C-j), vol.126, pp.19-24
, , pp.1020-1021, 1077.
, 4-dihydronaphthalen-1-yl)-2,2-dimethyl-5-nitro-1,3-dioxane (IV-2e)
, To a solution of 4-(nitromethyl)-1,2-dihydronaphthalene (0.5 mmol, 90 mg, 100 mol%, vol.1
, After evaporation of solvent under reduced pressure, the residue crude was purified by column chromatography on silica gel, ml CH 3 CN was added formaldehyde solution
, 4-dihydronaphthalen-1-yl)-2-nitropropane-1,3-diol (0.5 mmol, 125 mg, 100 mol%), p-toluenesulfonic acid (8 mg, 10 mol%),excess MgSO4(1 g) and 1.5 ml acetone. The mixture was heated to reflux for 15 h, after evaporation of solvent under reduced pressure, the residue crude was purified by column chromatography on silica gel
, 400 MHz, CDCl 3 )? 7.17-7.12 (m, 3H
CDCl 3 ) ?137.4 (C-2), MHz, vol.132, issue.101 ,
, 127.8 (C-b), vol.126, pp.23-27
, HRMS: calculated for C 16 H 19 NO 4 : 289.1314, not found
, , p.3413, 1080.
, 4-dihydronaphthalen-1-yl)-2,2-dimethyl-5-nitro-1,3-dioxane (0.5 mmol, 145 mg, 100 mol%) in DMF (1.5 ml) was added Cs 2 CO 3 (0.5 mmol, 163 mg, vol.3
OAc) 2 (5 mol%), and dppe (5 mol%), the mixture was stirred for 30 min at 120 o C under ,
After evaporation of solvent under reduced pressure (vacuum, 80 o C), the residue crude (346 mg) was purified by column chromatography on silica gel (eluent: Et 2 O:PE = 10:90) to afford the desired product (87 %, 105 mg), Aspect: white solid m, pp.107-116 ,
, 400 MHz, CDCl 3 ) ? 8.20 (d, J = 8.4 Hz, 1H, H-a), 7.88 (d, J = 7.5 Hz, 1H, H-d), 7.78 (d, J = 7.7 Hz, vol.1
CDCl 3 ) ? 135.1 (C-g), MHz, vol.134, issue.101 ,
, C-b), 125.5 (C-c), 126.5 (C-j), vol.125
, , p.282, 1071.
, Methyl 5-acetoxy-4-(3,4-dihydronaphthalen-1-yl)-4-nitropentanoate (IV-2f)
, After evaporation of solvent under reduced pressure, the residue crude was dissolved in 1.5 ml dichloromethane, and then acetic anhydride (1 mmol) and DMAP (10 mol%) was added, the mixture was stirred at r.t. for 2 h under Ar. After evaporation of solvent under reduced pressure, the final crude was purified by column chromatography on silica gel, p.254
, 400 MHz, CDCl 3 ) ? 7.19-7.06 (m, 3H, H-c,d,a), 6.96 (d, J = 7.0 Hz, 1H, H-b), vol.6
CDCl 3 ) ? 172.2 (C-8), 170.0 (C-11), 137.2 (C-2), MHz, vol.131, issue.101 ,
, 92.8 (C-1), 65.2 (C-10), vol.130
, HRMS: calculated for C 18 H 21 NO 6 : 347.1369, not found, pp.1065-1066, 1104.
, Tetrahedron, vol.51, issue.6, pp.1675-1684, 1995.
, 7-tetrahydro-4H-indol-4-one (5 mmol, 676 mg, 100 mol%), nitromethane (50 mmol, 1.53 g, 10 eq), N,N-dimethylethane-1,2-diamine (1.5 mmol, 132 mg, 30 mol%), and toluene (25 ml), the mixture was refluxed for 72 h. After evaporation of solvent under reduced pressure, the residue crude was purified by column chromatography on silica gel, vol.6
, Aspect: yellow solid, p.145
, 400 MHz, CDCl 3 ) ? 8.54 (s, 1H, H-NH), vol.7
,
CDCl 3 ) ? 149.3 (C-d), 139.0 (C-2), MHz, vol.127, issue.101 ,
, C-b), 26.5 (C-1), vol.104, pp.22-29
, HRMS: calculated for
, , pp.1018-1019, 1100.
, 7-dihydro-1H-indole (0.5 mmol, 89 mg, 100 mol%) in acetonitrile (1.5 ml) was added acetonitrile (2.5 mmol, 265 mg, 5 eq) and DBU(38 mg, p.50
, After evaporation of solvent under reduced pressure, the residue crude (410 mg) was purified by column chromatography on silica gel (eluent: EA:PE = 30:70) to afford the desired product (83 %, 118 mg, the mixture was stirred for 3 h at r.t. under Ar
CDCl 3 ) ? 8.21 (s, 1H, H-NH), 6.58 (t, J = 2.5 Hz, MHz, vol.1, issue.400 ,
,
CDCl 3 ) ? 130.4 (C-2), 129.5 (C-d), MHz, vol.119, issue.101 ,
, C-b), 94.1 (C-1), 30.8 (C-5), 24.2 (C-6), vol.112
, HRMS: calculated for C 15 H 16 N 4 O 2 : 284.1273
, , pp.1086-1087, 1348.