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R. Rezaei et al.: H -catalyzed three-component synthesis of 1,8-dioxo-decahydroacridine derivativesꢀ
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9-(3-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexa- 124.8, 131.5, 133.7, 147.4, 148.6, 150.7, 194.9. Anal. Calcd for C23H25ClNO4
hydro-1,8(2H,5H)-acridinedione (2h)ꢀThis compound was ob- (428.908): C, 64.41; H, 5.88. Found: C, 64.29; H, 5.74.
tained by Method B in the presence of thiourea; reaction time 60 min;
yield 75%; mp 287–289°C; IR (cm-1): 3276, 3050, 2957, 1642, 1604, 1476, 9-(2-Hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro-
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1217; H NMR (CDCl3): δ 1.13 (s, 6H), 1.26 (s, 6H), 2.41 (m, 8H), 3.76 1,8(2H,5H)-acridinedione (2q)ꢀThis compound was obtained by
(s, 3H), 5.54 (s, 1H), 6.69–7.23 (m, 4H), 11.98 (s, 1H); Mass: 381(M++2), Method A in the presence of ammonium acetate; reaction time 5 min;
380(M++1), 379 (M+, 97.4). Anal. Calcd for C24H29NO3 (379.492): C, 75.96; yield 95%; mp: >300°C; reported mp 310–312°C [35].
H, 7.70. Found: C, 80.08; H, 7.58.
10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-
9-(3-Nitrophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro- hexahydro-1,8(2H,5H)-acridinedione (2r)ꢀThis compound was
1,8(2H,5H)-acridinedione (2i)ꢀThis compound was obtained by obtained by Method A in the presence of 4-chloroaniline; reaction
Method A in the presence of ammonium acetate; reaction time 3 min; time 5 min; yield 95%; mp 309–311°C, IR (cm-1): 3050, 2956, 1633, 1574,
yield 80%. This compound was obtained by Method B in the pres- 1487, 1216, 695; 1H NMR (DMSO-d6): δ 0.72 (s, 6H), 0.89 (s, 6H), 1.89 (m,
ence of thiourea; reaction time 80 min; yield 75%; mp287–289°C; re- 4H), 2.20 (m, 4H), 5.04 (s, 1H), 7.09–7.70 (m, 9H).
ported mp 287–289°C [22].
10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(3-nitrophenyl)-
9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexa- 3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (2s)ꢀThis com-
hydro-1,8(2H,5H)-acridinedione(2j)ꢀThiscompoundwasobtained pound was obtained by Method A in the presence of 4-chloroaniline;
by Method A in the presence of ammonium acetate; reaction time reaction time 10 min; yield 80%; mp 297–299°C; IR (cm-1): 2950, 1634,
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7 min; yield 80%. This compound was obtained by Method B in the 1575, 1529, 1490, 1348, 1217; H NMR (CDCl3): δ 0.81 (s, 6H), 1.00 (s,
presence of thiourea; reaction time 65 min; yield 85%; mp 272–273°C; 6H), 2.00 (m, 4H), 2.19 (m, 4H), 5.36 (s, 1H), 7.29–8.20 (m, 8 Hz); 13C
reported mp 272–273°C [34].
NMR (CDCl3): 26.7, 29.7, 32.6, 32.8, 41.8, 50.0, 114.2, 121.3, 121.7, 128.9,
130.6, 131.1, 135.4, 135.8, 137.2, 148.1, 148.4, 150.1, 195.7. Anal. Calcd for
3,3,6,6-Tetramethyl-9-(2-naphthyl)-3,4,6,7,9,10-hexahydro- C29H29ClN2O4 (505.004): C, 68.97; H, 5.79. Found: C, 69.08; H, 5.87.
1,8(2H,5H)-acridinedione (2k)ꢀThis compound was obtained by
Method A in the presence of ammonium acetate; reaction time 15 10-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-(2-naphthyl)-
min; yield 85%; mp >300°C; IR (cm-1): 3280, 3054, 2952, 1647, 1603, 3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (2t)ꢀThis com-
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1485, 1214; H NMR (DMSO-d6), δ 0.86 (s, 6H), 1.02 (s, 6H), 2.08 (m, pound was obtained by Method A in the presence of 4-chloroaniline;
4H), 2.43 (m, 4H), 4.99 (s, 1H), 7.40–7.80 (m, 7H), 9.39 (s, 1H); 13C NMR reaction time 10 min; yield 80%; mp 270–273°C; IR (cm-1): 3050, 2956,
(DMSO-d6): 26.8, 29.6, 31.2, 32.6, 33.8, 50.7, 111.7, 125.5, 126.1, 126.2, 1632, 1575, 1489, 1217, 732; 1H NMR (CDCl3): δ 0.83 (s, 6H), 0.99 (s, 6H),
127.3, 127.6, 127.7, 128.0, 132.0, 133.2, 145.0, 149.9, 194.9. Anal. Calcd for 1.99 (m, 4H), 2.20 (m, 4H), 5.48 (s, 1H), 7.25–7.86 (m, 11H); 13C NMR
C27H29NO2 (399.525): C, 81.17; H, 7.32. Found: C, 81.03; H, 7.43.
(CDCl3): 26.8, 29.8, 32.5, 32.7, 41.9, 50.2, 114.8, 125.1, 125.5, 126.3, 126.6,
127.4, 127.8, 128.1, 132.3, 133.5, 135.5, 137.6, 143.3, 149.4, 195.8. Anal. Calcd
9-(2-Methoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexa- for C33H32ClNO2 (510.065): C, 77.71; H, 6.32. Found: C, 77.86; H, 6.25.
hydro-1,8(2H,5H)-acridinedione(2l)ꢀThiscompoundwasobtained
by Method A in the presence of ammonium acetate; reaction time 9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-(3-nitrophenyl)-
6 min; yield 80%; mp 293–295°C; reported mp 293–295°C [35].
3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (2u)ꢀThis com-
pound was obtained by Method A in the presence of 3-nitroaniline;
3,3,6,6-Tetramethyl-9-(2-nitrophenyl)-3,4,6,7,9,10-hexahydro- reaction time 6 min; yield 90%; mp269–272°C; reported mp 276–
1,8(2H,5H)-acridinedione (2m)ꢀThis compound was obtained 278°C [24].
by Method A in the presence of ammonium acetate; reaction time
10 min; yield 95%; mp 290–292°C; reported mp 293–295°C [36].
9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-
hexahydro-1,8(2H,5H)-acridinedione (2v)ꢀThis compound was
4-(3,3,6,6-Tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8,9,10-decahydro- obtained by Method A in the presence of aniline; reaction time
9-acridinyl)-benzonitrile (2n)ꢀThis compound was obtained by 20 min; yield 95%; mp 220–222°C; reported mp 220–222°C [24].
Method A in the presence of ammonium acetate; reaction time 3 min;
yield 95%; mp >300°C; reported mp 324–326°C [25].
3,3,6,6-Tetramethyl-9,10-diphenyl-3,4,6,7,9,10-hexahydro-
1,8(2H,5H)-acridinedione (2w)ꢀThis compound was obtained
9-(2-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydro- by Method A in the presence of aniline; reaction time 40 min; yield
1,8(2H,5H)-acridinedione (2o)ꢀThis compound was obtained by 90%; mp 252–254°C; reported mp 254–256°C [37].
Method A in the presence of ammonium acetate; reaction time 5 min;
yield 95%; mp 220–222°C; reported mp 220–222°C [36].
9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-
hexahydro-1,8(2H,5H)-acridinedione (2x)ꢀThis compound was
9-(4-Chloro-3-nitrophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10- obtained by Method A in the presence of aniline; reaction time
hexahydro-1,8(2H,5H)-acridinedione (2p)ꢀThis compound was 10 min; yield 80%; mp 244–246°C; reported mp 244–246°C [38].
obtained by Method A in the presence of ammonium acetate; reac-
tion time 15 min; yield 90%; mp >300°C; IR (cm-1): 3280, 3052, 2958, 3,3,6,6-Tetramethyl-9-(3-nitrophenyl)-10-phenyl-3,4,6,7,9,10-
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1643, 1596, 1524, 1487, 1358, 1219; H NMR (DMSO-d6): δ 0.88 (s, 6H), hexahydro-1,8(2H,5H)-acridinedione (2y)ꢀThis compound was
1.02 (s, 6H), 2.09 (m, 4H), 2.43 (m, 4H), 4.87 (s, 1H), 7.48–7.73 (m, 3H), obtained by Method A in the presence of aniline; reaction time
9.50 (s, 1H);13C NMR (DMSO-d6): 27.0, 29.4, 32.7, 33.9, 50.4, 110.6, 122.5, 10 min; yield 85%; mp 297–299°C; reported mp 297–299°C [37].
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