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1 SUPPRTIG IFRMATI Silver-catalyzed furoquinolines synthesis: From nitrogen effects to the use of silver imidazolate polymer as a new and robust silver catalyst Evelyne Parker, a icolas Leconte, b Thomas Godet, a and Philippe Belmont* a,b a University of Lyon and CRS, UMR 5246 ICBMS, Laboratoire de Synthèse et Méthodologie rganiques, 43 Boulevard du 11 ovembre 1918, Villeurbanne (Lyon), France. b Institut Curie and CRS, UMR 176 CSVB, Team rganometallic Chemistry, Heterocycles and Biological targets, Institut Curie, 26 rue d'ulm, Paris cedex 05, France. Fax : +33 (0) , Tel : +33 (0) , Philippe.Belmont@curie.fr, url:
2 General methods: General procedure for the AgTf-catalyzed cyclization/acetalization tandem reaction. Silver triflate (5 mol%) was added in one portion to a solution of 2-alkynyl-3- carbaldehyde quinoline (0.1 mmol) in,-diethylaminoethanol (2 ml, 0.05M) under argon. The mixture was stirred at r.t. until completion of the reaction (TLC monitoring) and filtered through celite. The celite pad was abundantly washed with dichloromethane (20 ml) and the filtrate was washed with sat. aq. solution of ahc 3 ( 3) and brine. The organic layer was then dried over a 2 S 4, filtered and concentrated under reduced pressure. Flash chromatography on silica gel (c-hexane / EtAc (1%Et 3 ); 9 : 1 to 0 : 1) afforded the desired furoquinoline. General procedure for the Ag 2 -catalyzed cyclization/acetalization tandem reaction. Silver(I) oxide (5 mol%) was added in one portion to a solution of 2-alkynyl-3- carbaldehyde quinoline (0.1 mmol) in,-diethylaminoethanol (2 ml, 0.05M) under argon. The mixture was stirred at r.t. until completion of the reaction (TLC monitoring) and filtered through celite. The celite pad was abundantly washed with dichloromethane (20 ml) and the filtrate was washed with a saturated aqueous solution of ahc 3 ( 3) and brine to afford the desired compound. Representative procedure for the [Ag(Im)] n -catalyzed cyclization/acetalization tandem reaction, compound (12). A,-diethylaminoethanol solution (1 ml) containing [Ag(Im)] n (1.7 mg, 9.7 mol, 5 mol%) and PPh 3 (2.6 mg, 9.7 mol, 5 mol%) is vigorously stirred during 30 min at r.t. and the 2-phenylalkynyl-3- carbaldehyde quinoline 1 (47.0 mg, 0.2 mmol) is added in one portion. After 30 min (TLC monitoring) the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Flash chromatography on basic alumina (c- Hexane / EtAc ; 8 : 2 to 0 : 1) afforded the desired furoquinoline 12 (68 mg, 100%) as a yellow oil. 1 The detailed experimental procedure for the quinolines starting materials and compounds 1-6 can be found in : - A. Patin, P. Belmont Synthesis 2005, (14), T. Godet, C. Vaxelaire, C. Michel, A. Milet and P. Belmont, Chem.--Eur. J., 2007, 13,
3 (7) Yellow oil. H (300 MHz; CDCl 3 ) (2H, m, CH 2(cyclopropyl) ), (2H, m, CH 2(cyclopropyl) ), 1.04 (6H, t, J 7.2, (CH 2 -CH 3 ) 2 ), (1H, m, CH (cyclopropyl) ), 2.61 (4H, q, J 7.2, (CH 2 -CH 3 ) 2 ), 2.79 (2H, t, J 6.3, -CH 2 -CH 2 -), (2H, m, -CH 2 -CH 2 -), 5.33 (1H, d, J 10.2, C=CH-CH), 6.62 (1H, s, CH-), 7.50 (1H, ddd, J 1.2 and 6.9 and 8.1, H Ar ), 7.71 (1H, ddd, J 1.5 and 6.9 and 8.4, H Ar ), 7.82 (1H, dd, J 1.2 and 8.1, H Ar ), 8.06 (1H, d, J 8.4, H Ar ) and 8.16 (1H, s, H Ar ); C (75 MHz; CDCl 3 ) 7.8, 8.0, 8.8, 11.8, 47.7, 52.4, 66.1, 103.4, 107.4, 126.4, 127.6, 128.6, 129.0, 129.3, 130.5, 131.6, 149.9, and 153.9; max /cm and 2926 (C-H), 1623 (C=C), 1308 (C=), 1065 (C-) and 1027 (C-); HRMS (ESI+): m/z calcd for [C 21 H ] + : ; found: (8) Yellow oil. H (300 MHz; CDCl 3 ) 1.05 (6H, t, J 7.2, (CH 2 -CH 3 ) 2 ), 1.31 (9H, s, C(CH 3 ) 3 ), 2.62 (4H, q, J 7.2, (CH 2 -CH 3 ) 2 ), 2.79 (2H, t, J 7.3, -CH 2 -CH 2 -), 3.84 (2H, t, J 6.3, -CH 2 -CH 2 -), 5.83 (1H, s, CH-t-Bu), 6.59 (1H, s, CH-), 7.51 (1H, ddd, J 1.2 and 6.9 and 8.1, H Ar ), 7.72 (1H, ddd, J 1.2 and 6.9 and 8.4, H Ar ), 7.83 (1H, d, J 8.1, H Ar ), 8.10 (1H, d, J 8.7, H Ar ) and 8.17 (1H, s, H Ar ); C (75 MHz, CDCl 3 ) 11.8, 30.5, 31.9, 47.7, 52.4, 65.8, 103.5, 112.0, 126.5, 127.7, 128.6, 129.4, 130.5, 131.5, 148.8, and 155.1; max /cm (C-H), 1625 and 1504 (C=C), 1069 (C-) and 1023 (C-); HRMS (ESI+): m/z calcd for [C 22 H ] + : found: (9) Yellow oil. H (300 MHz; CDCl 3 ) 1.02 (6H, t, J 7.1, (CH 2 -CH 3 ) 2 ), 2.58 (4H, q, J 7.1, (CH 2 -CH 3 ) 2 ), 2.74 (2H, t, J 6.3, -CH 2 -CH 2 -), 3.41 (3H, s, CH 3 ), (2H, m, -CH 2 -CH 2 -), (2H, m, CH 2 -CH 3 ), 5.93 (1H, t, J 7.3, CH-CH 2 -CH 3 ), 6.60 (1H, s, CH- ), 7.54 (1H, ddd, J 1.0 and 7.0 and 8.2, H Ar ), 7.75 (1H, ddd, J 1.5 and 7.0 and 8.5, H Ar ), 7.85 (1H, d, J 8.2, H Ar ), 8.13 (1H, d, J 8.5, H Ar ) and 8.19 (1H, s, H Ar ); C (75 MHz, CDCl 3 ) 11.6, 47.7, 52.3, 57.9, 62.3, 66.3, 97.4, 104.1, 127.0, 127.9, 128.6, 129.3, 129.7, 130.7, 131.6, 150.0, and 153.5; max /cm , 2926, 2874 and 2817 (C-H), 1624 and 1505 (C=C), 1115 and 1074 (C- and C-) ; HRMS (CI): m/z calcd for [C 20 H ] + : ; found:
4 (10) range oil. H (300 MHz; CDCl 3 ) 1.05 (6H, t, J 7.2, (CH 2 - CH 3 ) 2 ), (6H, m, 3 x CH 2(THP) ), 2.62 (4H, q, J 7.2, (CH 2 - CH 3 ) 2 ), 2.78 (2H, br s, -CH 2 -CH 2 -), (1H, m, H 5b(THP) ), (3H, m, H 5a(THP) and -CH 2 -CH 2 -), (2H, m, =CH-CH 2 -), 4.79 (1H, dd, J 3.0 and 6.3, H 1(THP) ), 5.96 (1H, t, J 7.5, =CH-CH 2 ), 6.60 (1H, s, CH-), 7.54 (1H, ddd, J 1.5 and 6.9 and 8.1, H Ar ), 7.74 (1H, ddd, J 1.2 and 6.9 and 8.4, H Ar ), 7.85 (1H, d, J 8.1, H Ar ), 8.12 (1H, d, J 8.4, H Ar ) and 8.20 (1H, s, H Ar ); C (75 MHz; CDCl 3 ) 11.6, 19.5, 25.7, 30.8, 47.7, 52.3, 61.1, 62.2, 66.3, 97.8, 104.1, 127.0, 127.9, 128.6, 129.4, 129.7, 130.6, 131.6, 150.0, and 153.6; max /cm and 2871 (C-H), 1623 and 1505 (C=C), 1312 (C=), 1114 and 1075 (C-) and 1021 (C-); HRMS (ESI+): m/z calcd for [C 24 H ] + : ; found: (11) Yellow oil. H (400 MHz; CDCl 3 ) 1.02 (6H, t, J 7.2, (CH 2 - CH 3 ) 2 ), 2.31 (3H, s, CH 3 ), 2.57 (4H, q, J 7.2, (CH 2 -CH 3 ) 2 ), 2.74 (2H, t, J 6.3, -CH 2 -CH 2 -), 3.48 (2H, dd, J 2.8 and 7.4, =CH- CH 2 ), 3.61 (1H, d, J 13.2, CH a H b Ph), 3.66 (1H, d, J 13.2, CH a H b Ph), (2H, m, -CH 2 -CH 2 -), 5.99 (1H, t, J 7.4, =CH-CH 2 ), 6.59 (1H, s, CH-), 7.24 (1H, d, J 7.1, H Ar ), 7.31 (2H, dd, J 7.1 and 7.2, H Ar ), 7.38 (2H, d, J 7.2, H Ar ), 7.53 (1H, ddd, J 1.1 and 6.9 and 8.1, H Ar ), 7.74 (1H, ddd, J 1.4 and 6.9 and 8.6, H Ar ), 7.84 (1H, d, J 8.1, H Ar ), 8.14 (1H, d, J 8.6, H Ar ) and 8.18 (1H, s, H Ar ); C (100 MHz; CDCl 3 ) 11.9, 42.2, 47.7, 52.2, 52.4, 61.6, 66.3, 98.1, 103.7, 126.8, 127.0, 127.8, 128.3, 128.6, 129.2, 129.4, 129.6, 130.6, 131.6, 139.4, 150.0, and 153.7; max /cm , 2931 and 2788 (C-H), 1625 and 1505 (C=C), 1310 (C=), 1122 (C-) and 1073 (C- ); HRMS (ESI+): m/z calcd for [C 27 H ] + : ; found: (12) yellow oil. H (300 MHz; (CDCl 3 ) 1.03 (6H, t, J 7.1, (CH 2 -CH 3 ) 2 ), 2.60 (4H, q, J 7.1, (CH 2 -CH 3 ) 2 ), 2.79 (2H, t, J 6.3, -CH 2 -CH 2 -), (2H, m, -CH 2 -CH 2 -), 6.72 (1H, s, =CH-Ph), 6.75 (1H, s, CH-), 7.24 (1H, ddd, J 1.1 and 7.3 and 7.3, H Ar ), 7.39 (2H, dd, J 7.3 and 7.9, H Ar ), 7.51 (1H, ddd, J 1.1 and 6.9 and 8.2, H Ar ), 7.73 (1H, ddd, J 1.4 and 6.9 and 8.5, H Ar ), 7.82 (1H, dd, J 1.1 and 8.2, H Ar ), 7.89 (2H, dd, J 1.3 and 7.9, H Ar ), 8.15 (1H, d, J 8.5, H Ar ) and 8.18 (1H, s, H Ar ); C (125 MHz; (CD 3 ) 2 C) 12.2, 48.3, 53.2,
5 68.0, 100.9, 106.2, 127.5, 127.6, 128.7, 129.3, 129.7, 129.9, 130.0, 130.1, 131.4, 132.6, 136.3, 150.7, and 155.1; max /cm and 2834 (C-H), 1620 and 1489 (C=C),1234 (C=), 1110 (C-) and 1026 (C-); HRMS (ESI+): m/z calcd for [C23H ] + : ; found : (13) Yellow oil. H (300 MHz; CDCl 3 ) 1.00 (6H, t, J 7.2, (CH 2 -CH 3 ) 2 ), 2.57 (4H, q, J 7.2, (CH 2 -CH 3 ) 2 ), 2.76 (2H, t, J 6.3, -CH 2 -CH 2 -), (2H, m, -CH 2 -CH 2 -), 6.78 (1H, s, CH-), 6.97 (1H, s, =CH-C 5 H 5 ), 7.07 (1H, ddd, J 1.0 and 4.9 and 7.4, H Ar ), 7.53 (1H, ddd, J 1.0 and 7.0 and 8.0, H Ar ), 7.66 (1H, ddd, J 1.8 and 7.4 and 7.4, H Ar ), 7.74 (1H, ddd, J 1.4 and 7.0 and 8.4, H Ar ), 7.83 (1H, dd, J 1.0 and 8.0, H Ar ), 8.14 (1H, d, J 7.4, H Ar ), 8.16 (1H, d, J 8.4, H Ar ), 8.21 (1H, s, H Ar ) and 8.61 (1H, d, J 4.9, H Ar ); C (75 MHz; CDCl 3 ) 11.7, 47.6, 52.4, 66.7, 101.7, 105.4, 121.0, 124.2, 127.2, 127.9, 128.6, 128.7, 129.9, 130.8, 131.5, 136.1, 149.6, 150.2, 153.3, and 154.8; max /cm and 2808 C-H), 1582 and 1465 (C=C), 1341 (C=), 1099 and 1070 (C- and C-) HRMS (ESI+): m/z calcd for [C 23 H a] + : ; found: (14) Yellow oil. H (300 MHz; CDCl 3 ) 1.03 (6H, t, J 7.1, (CH 2 -CH 3 ) 2 ), 2.58 (4H, q, J 7.1, (CH 2 -CH 3 ) 2 ), 2.78 (2H, t, J 6.4, -CH 2 -CH 2 -), (2H, m, -CH 2 -CH 2 -), 3.98 (3H, s, -CH 3 ) 6.75 (1H, s, CH-), 6.91 (1H, dd, J 0.8 and 8.2, H Ar ), 7.02 (1H, ddd, J 0.8 and 7.6 and 7.8, H Ar ), 7.23 (1H, ddd, J 1.7 and 7.6 and 8.2, H Ar ), 7.25 (1H, s, =CH-(2-Me- Ph)), 7.52 (1H, ddd, J 1.1 and 6.9 and 8.1, H Ar ), 7.74 (1H, ddd, J 1.4 and 6.9 and 8.4, H Ar ), 7.84 (1H, dd, J 1.4 and 8.1, H Ar ), 8.18 (1H, d, J 8.4, H Ar ), 8.19 (1H, s, H Ar ) and 8.35 (1H, dd, J 1.7 and 7.8, H Ar ); C (75 MHz; CDCl 3 ) 11.4, 47.5, 52.2, 55.6, 66.1, 94.8, 104.7, 110.4, 120.6, 124.2, 126.6, 127.7, 128.1, 128.6, 128.7, 129.6, 130.0, 130.6, 131.5, 150.2, 150.7, and 157.0; max /cm , 2932 and 2834 (C-H), 1620 and 1489 (C=C), 1234 (C=), 1110 (C-) and 1055 (C-); HRMS (ESI+): m/z calcd for [C 25 H ] + : ; found:
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