Doles Synthesis in Presence of Marine Sponge/ H3POTable 2. Solvent-free Fischer-indole Reaction of Phenylhydrazine With Cyclohexanone as Ketone, inside the Presence of Unique Catalysts Catalysts Marine sponge/H3PO4 [cmmim] [BF4] (12) Propylphosphonic Anhydride (20) PPA (16) Time, min five five 120 15 Yield, 90 90 89 92 Condition r.t. MW, 100 14095As the results indicate, marine sponge/H3PO4 are much more advantageous more than previously applied catalysts, that are as follows: requirement of a very little quantity of the catalyst, mild reaction, area temperature, fantastic solid absorbent , simple to manage, and solutions in good-to-high yields. Far more importantly, this catalyst created enantioselective solutions with high enantiomeric excess, as shown in Table 1 (entries 2 and 3). Structures from the products had been characterized by their spectral (1H NMR, IR, and MS) information (27, 28). Selected spectral data for the solutions in Table 1 are provided: 6,7,eight,9-tetrahydro-5H-carbazole (14-15)-(entry 1): IR(cm-1, KBr): 3396 (-NH), 1614, 1583 (C=C), 738, 635 (aromatic), 1H NMR (400 MHz, CDCl3, TMS, ppm): 7.Price of 945652-35-7 67 (1H, bs, NH), 7.55 (1H, d, J=7.52), 7.41(1H, d, J=7.91), 7.22 (1H, t, J=7.75), 7.05 (1H, t, J=7.1), two.9 (2H, t, CH2, J=3.1), 2.7 (2H, t, CH2, J=5.two), 1.8 (4H, m, 2CH2); 13C NMR (400 MHz, CDCl3, TMS, ppm): 136.1, 134.1, 127.7, 121.1, 119.0, 117.7, 110.three, 109.0, 24.7, 22.9, 22.0, 21.2. 3-Methyl-2,3,four,9-Tetrahydro-1H-carbazole-(entry 2): IR(cm-1, KBr): 3396 (-NH), 1619, 1583 (C=C), 740, 635 (aromatic), 1H NMR (400 MHz, CDCl3, TMS, ppm): 7.six (1H, bs,Jundishapur J Nat Pharm Prod. 2013;eight(4)five. Discussion5.1. Characterization of ProductsNH), 7.five (1H, d, J=7.five Hz), 7.38 (1H, d, J=7.95 Hz), 7.25 (1H, t, J=7.7 Hz), 7.03 (1H, t, J=7.1 Hz), two.9 (2H, t, CH2, J=9 Hz), two.7 (2H, d, CH2, J=6.5 Hz), 2.1 (2H, m, CH2), 1.6 (1H, m), 1.2 (3H, d, CH3, J= 6.45 Hz); 13C NMR (400 MHz, CDCl3, TMS, ppm): 135.7, 134.1, 128.eight, 124.1, 119.0, 117.7, 111.four, 110.0, 30.9, 29.0, 28.three, 26.two, 21.7. 3-Phenyl-2,3,4,9-Tetrahydro-1H-carbazole-(entry 3): IR(cm-1, KBr): 3396 (-NH ), 1644, 1604 (C=C), 749, 682 (aromatic), 1H NMR (400 MHz, CDCl3, TMS, ppm): 7.65 (1H, bs, NH), 7.54 (1H, d, J=7.55 Hz), 7.45 (1H, d, J=8 Hz), 7.36 (1H, t, J=7.7 Hz), 7.30 (1H, t, J=7.0 Hz), 7.two (2H, t, J= eight.1 Hz), 7.15 (3H, m), three.0 (2H, d, CH2, J=11 Hz), two.eight (2H, d, CH2, J=6.9), 2.two (2H, m, CH2), 1.9 (1H, m); 13C NMR (400 MHz, CDCl3, TMS, ppm): 145.eight, 136.0 , 135.7, 132.90, 132.92, 128.9,126.7, 126.8, 124.9, 124.1, 119.0, 117.7, 111.4, 110.0, 38.0, 32.(4-Aminobutyl)dimethylamine supplier three, 30.PMID:23376608 3, 26.8. 1,2,3,4-Tetrahydrocyclopenta[b]indole (14-15)-(entry 4): IR(cm-1, KBr): 3402 (-NH ), 1600, 1502 (C=C), 749, 693 (aromatic), 1H NMR (400 MHz, CDCl3, TMS, ppm): 7.59 (1H, bs, NH), 7.45 (1H, d, J=7.15 Hz), 7.33 (1H, d, J=7.05 Hz), 7.two (1H, t, J=7.4 Hz), 7.05 (1H, t, J=7.25 Hz), three.0 (2H, t, CH2, J=7 Hz), 2.six (2H, t, CH2, J=7 Hz), 1.59 (2H, p, CH2, J=7 Hz);13C NMR (400 MHz, CDCl3, TMS, ppm): 137.0, 135.6, 125.eight, 122.0, 120.8, 120.0, 112.1, 111.0, 26.9, 25.eight, 24.9. six,7,8,9,ten,11-Hexahydrocycloocta[b]indole (14-15)-(entry 5): IR(cm-1, KBr): 3391 (-NH ), 1619, 1599 (C=C), 743, 698 (aromatic), 1H NMR (400 MHz, CDCl3, TMS, ppm): 7.five (1H, bs, NH), 7.49 (1H, d, J=7.3 Hz), 7.35 (1H, d, J=7.55 Hz), 7.2 (1H, t, J=7.1 Hz), 7.04 (1H, t, J=7.45 Hz), 2.75-2.85 (4H, d, 2CH2), two.52.65 (4H, m, 2CH2), two.1 (4H, m, 2CH2); 13C NMR (400 MHz, CDCl3, TMS, ppm): 136.6, 135.1, 129.7, 124.7, 119.0, 117.7, 112.6, 110.4, 28.six, 26.5, 26, 25.9, 25.7, 22.two. 5,six,11,12-Tetrahydro-6,12-diaza-indeno[1,2-b]fluor.