Reaction of ethyl diazoacetate with N-2,7-octadienylanilines catalyzed by compounds of copper

Fakhretdinov, R. N.; Marvanov, R. M.; Джемилев, У. М.; Толстиков, Г. А.

doi:10.1007/bf00953026

Cited by 1 publication

(4 citation statements)

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“…This was then dissolved in toluene (5 ml) and Amberlyst ® (110 mg) added and the mixture heated at reflux overnight. The reaction mixture was filtered, the filtrate concentrated in vacuo and then purified on silica eluting with ethyl acetate-light petroleum (1 : 4) (50), 125 (21), 94 (43), 78 (80), 44 (19).…”

Section: Methyl 37-dimethyl-1-(2-phenylsulfonylethyl)indole-2-carboxy...mentioning

confidence: 99%

“…H 21 NO 5 S ϩ H requires 388.1219); ν max (film)/cm Ϫ1 3448, 2951, 1733, 1701, 1350, 1306, 1232, 1159, 1087, 769, 534; δ H (300 MHz; CDCl 3 ) 7.97 (2H, m, PhH), 7.70 (1H, m, PhH), 7.61 (2H, m, PhH), 7.20 (1H, d, J 8.0, ArH), 7.02 (1H, ∼t, J 8.0, H-5), 6.70 (1H, d, J 8.0, ArH), 5.04 (2H, m, NCH 2 ), 3.86 (3H, s, Me), 3.84 (3H, s, Me), 3.73 (2H, m, NCH 2 CH 2 ), 2.48 (3H, s, Me); δ C (75 MHz; CDCl 3 ) 162.7, 147.3, 139.5, 133.7 (CH), 129.5, 129.3 (CH), 128.1 (CH), 124.8, 122.1, 120.6 (CH), 113.2 (CH), 105.6 (CH), 57.0 (Me), 55.2 (Me), 51.6 (CH 2 ), 41.4 (CH 2 ), 10.9 (Me); 1 C unobserved; m/z (EI) 387 (M ϩ , 15%), 248 (78), 220 (100), 186 (50), 125 (21), 94 (43), 78 (80), 44(19).…”

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confidence: 99%

“…, 2848, 1729, 1584; δ H (300 MHz; CDCl 3 ) 7.23 (1H, dd, J 8.1, 0.9, ArH), 7.01 (1H, t, J 7.8, ArH), 6.71 (1H, d, J 7.8, ArH), 4.28 (3H, s, OMe), 3.93 (6H, s, NMe, OMe), 2.53 (3H, s, Me); δ C (100 MHz; CDCl 3 ) 163.4, 148.0, 129.3, 129.2, Recrystallised (light petroleum), mp 90-92 ЊC (Found: C, 66.7; H, 6.7; N, 5.9. C 13 H 15 NO 3 requires C, 66.9; H, 6.5; N, 6.0%); ν max (KBr)/cm Ϫ1 2999, 2980, 2841, 1703, 1611, 1578; δ H (300 MHz; CDCl 3 ) 7.22 (1H, t, J 8.1, ArH), 6.91 (1H, d, J 8.4, ArH), 6.44 (1H, d, J 7.7, ArH), 3.94 (3H, s, OMe), 3.93 (3H, s, OMe), 3.92 (3H, s, NMe), 2.77 (3H, s, Me); δ C (100 MHz; CDCl 3 ) 163.6, 156.7, 140.5, 126,0 (CH), 123.9, 122.0, 117.3, 103.0 (CH), 99.3 (CH), 55.1 (Me), 51.2 (Me), 32.3 (Me), 12.8 (Me); m/z (EI) 233 (M ϩ , 100%), 219 (8), 218 (69), 174(19), 130(23), 89(34).Methyl 1,3-dimethyl-6-methoxyindole-2-carboxylate 4d2 . Recrystallised (light petroleum) to give a colourless crystalline solid, mp 93-94 ЊC; (Found : C, 66.9; H, 6.7; N, 5.9); ν max (KBr)/ cm Ϫ1 3019, 2954, 2848, 1710, 1637, 1571; δ H (300 MHz; CDCl 3 ) Method 1 gave only starting material.…”

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confidence: 99%

“…The reaction mixture was then concentrated in vacuo and purified on silica eluting with ethyl acetate-light petroleum (1 : 10) to give the title compound (6.63 g, 88%) as an orange crystalline solid, mp49-50 ЊC (Found: MH ϩ , 270.1492. C 17 H 19 NO 2 ϩ H requires 270.1494); ν max (KBr)/cm Ϫ1 3447, 3392, 1720, 1618, 1522, 1321, 1186, 796, 723 (ArH); δ H (300 MHz; CDCl 3 ) 7.36 (5H, m, PhH), 7.01 (2H, d, J 8.5, ArH), 6.56 (2H, d, J 8.5, ArH), 5.15 (2H, s, CH 2 ), 3.47 (2H, t, J 6.3, NCH 2 ), 2.68 (2H, t, J 6.3, NCH 2 CH 2 ), 2.25 (3H, s, Me); NH not observed; δ C (75 MHz; CDCl 3 ) 172.1, 135.6, 129.8 (CH), 128.6 (CH), 128.4, 128.3 (CH), 128.2 (CH), 128.1, 114.0 (CH), 66.5 (CH 2 ),40.4 (CH 2 ), 33.6 (CH 2 ), 20.4 (Me); m/z (CI) 270 (MH ϩ , 32%), 135(20), 120(46), 108 (100), 91 (70), 78(19). -anisidine (333 mg, 2.7 mmol) and benzyl acrylate (500 mg, 3.0 mmol) in EtOH (15 ml) was heated at reflux for 3 days.…”

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confidence: 99%

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N–H Insertion reactions of rhodium carbenoids. Part 3.1 The development of a modified Bischler indole synthesis and a new protecting-group strategy for indoles

Bashford

Cooper

Kane

et al. 2002

J. Chem. Soc., Perkin Trans. 1

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A modified version of the Bischler indole synthesis has been developed in which the key step is the N-H insertion reaction of rhodium carbene intermediates derived from α-diazo-β-ketoesters with anilines. Thus N-methylanilines 1 react with diazoketoesters 2 in the presence of dirhodium() acetate to give (N-arylamino)ketones 3, cyclisation of which using boron trifluoride-ethyl acetate or acidic ion exchange resin gives the indoles 4. In order to extend this method to the synthesis of N-unsubstituted indoles, a new protecting group strategy for indoles was developed. In this, anilines are reacted with α,β-unsaturated-esters or -sulfones to give the conjugate addition products 6 and 9, cyclisation of which gives indoles 8 and 11. The N-(2-ethoxycarbonylethyl)-and -(2-sulfonylethyl)-protecting groups are readily removed from indoles 8 and 11 by treatment with base.

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