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Yield 92%; mp 252C256 C; 1H NMR (600 MHz, DMSO-8

Yield 92%; mp 252C256 C; 1H NMR (600 MHz, DMSO-8.68 (s, 1H), 7.62 (d, = 7.8 Hz, 1H), 7.54 (d, = 7.8 Hz, 1H), 7.32 (t, 1H), 7.26 (t, 1H); 13C NMR (150 MHz, DMSO-210.5, 181.1, 172.5, 144.6, 140.4, 134.7, 131.4, 128.9, 127.3, 117.2; HRMS-ESI(?) calcd for C11H6NO3S2 263.9789 [M ? Na]?, found Moxalactam Sodium 263.9829. (Z)-Methyl 4-((2-oxo-4-thioxothiazolidin-5-ylidene)methyl)-benzoate (60) Prepared from methyl 4-formylbenzoate following the general process C. process A. Yield 58%; mp 171C173 C; 1H NMR (600 MHz, DMSO-8.24C8.26 (m, 3H), 7.81 (d, = 7.2 Hz, 2H), 7.63 (br, 2H); 13C NMR (150 MHz, DMSO-194.6, 148.4, 148.0, 132.3, 131.9, 124.3, 123.7, 118.9; HRMS-ESI(?) calcd for C10H6N3O2S 232.0259 [M ? H]?, found 232.0181. (E)-3-(4-Bromophenyl)-2-cyanoprop-2-enethioamide (12) Prepared from 4-bromobenzaldehyde following the general process A. Yield 59%; mp 176C179 C; 1H NMR (600 MHz, DMSO-10.13 (s, 1H), 9.64 (s, 1H), 8.01 (s, 1H), 7.84 (d, = 8.4 Hz, 2H), 7.77 (d, = 8.4 Hz, 2H); 13C NMR (150 MHz, DMSO-192.7, 146.0, 133.0, 132.5, 131.8, 126.4, 116.7, 113.8; HRMS-ESI(?) calcd for C10H6BrN2S 264.9435 [M ? H]?, found 264.9444. (E)-4-(3-Amino-2-cyano-3-thioxoprop-1-en-1-yl)benzoic Acid (13) Prepared from 4-formylbenzoic acid following the Moxalactam Sodium general process A. Yield 63%; mp 300 C; 1H NMR (600 MHz, DMSO-13.12 (s, 1H), 10.06 (s, 1H), 9.51 (s, 1H), 8.18 (s, 1H), 7.98 (d, = 8.4 Hz, 2H), 7.87 (d, = 8.4 Hz, 2H); 13C NMR (150 MHz, DMSO-192.2, 167.3, 161.9, 151.8, 140.1, 138.0, 132.6, 130.2, 128.5, 115.3; HRMS-ESI(?) calcd for C11H7N2O2S 231.0228 [M Moxalactam Sodium ? H]?, found 231.0257. (E)-N-(4-(3-Amino-2-cyano-3-thioxoprop-1-en-1-yl)phenyl)-acetamide (14) Prepared from 10.36 (s, 1H), 9.98 (s, 1H), 9.48 (s, 1H), 8.01 (s, 1H), 7.92 (d, = 8.9 Hz, 2H), 7.73 (d, = 8.9 Hz, 2H), 2.07 (s, 3H); 13C NMR (150 MHz, DMSO-193.2, 169.7, 147.4, 143.7, 132.4, 126.8, 119.5, 117.4, 110.4, 24.8; HRMS-ESI(+) calcd for C12H12N3SO 246.0701 [M + H]+, found 246.0705. (E)-2-Cyano-3-(1H-indol-5-yl)prop-2-enethioamide (15) Prepared from 111.58 (s, 1H), 9.90 (s, 1H), 9.41 (s, 1H), 8.24 (d, = 10.2 Hz, 2H), 7.81 (d, = 8.4 Hz 1H), 7.53 (d, = 7.8 Hz, 1H), 7.48C7.47 (m, 1H), 6.59 (s, 1H); 13C NMR (150 MHz, DMSO-193.7, 150.6, 138.8, 128.6, 128.3, 125.8, 123.9, 123.4, 118.1, 113.1, 108.3, 103.5; HRMS-ESI(+) calcd for C12H10N3S 228.0595 [M + H]+, found 228.0581. (E)-2-Cyano-3-(naphthalen-2-yl)prop-2-enethioamide (16) Prepared from 2-naphthaldehyde following the general process A. Yield 67%; mp 141C144 C; 1H NMR (600 MHz, DMSO-10.13 (s, 1H), 9.66 (s, 1H), 8.44 (s, 1H), 8.23 (s, 1H), 8.09C8.05 (m, 2H), 8.02 (d, = 7.8 Hz, 1H), 7.99 (d, = 8.4 Hz, 1H), 7.66 (t, = 7.2 Hz, 1H), 7.61 (t, = 7.2 Hz, 1H); 13C NMR (150 MHz, DMSO-193.1, 147.6, 134.9, 133.1, 130.2, 129.7, 129.5, 129.3, 128.5, 127.9, 125.5, 117.1, 113.1; HRMS-ESI(+) calcd for C14H11N2S 239.0643 [M + H]+, found 239.0650. 3-Phenyl-2-thioxo-imidazolidin-4-one (27).54 A suspension of methylglycinate hydrochloride (2.5 g, 20 mmol), phenylisothiocyanate (2.7 g, 20 mmol), and triethylamine (2.02 g, 2.8 mL, 20 mmol) in dry ethylacetate was refluxed (80 C) for 2 days. Solvent was evaporated under reduced pressure. The residue was dissolved in EtOH, and crystallization afforded 27 (3.5 g, 18 mmol, 92%) as a brown solid. 1H NMR (600 MHz, CDCl3) 7.53C7.46 (m, 3H), 7.33C7.32 (m, 2H), 4.23 (s, 2H). Synthesis of 1-Benzyl-2-thiohydantoin (28) A suspension of 11.84 (s, 1H), 7.27C7.36 (m, 5H), 4.85 (s, 2H), 4.07 (s, 2H). 4-Thioxo-thiazolidin-2-one (30).55 To a solution of compound 29 (0.61 g, 5.21 mmol) in dry toluene (12 mL) was added Lawessons reagent (2.2 g, 5.2 mmol). The reaction combination was Rabbit Polyclonal to LIPB1 refluxed for 2 h and cooled to room heat. The solid created was filtered off and crystallized from acetone to afford 0.64 g (98%) of 30 as yellow crystals. 1H (600 MHz, DMSO-13.58 (s, 1H), 4.67 (s, 2H). General Process B for Aldol Condensation.56 An aromatic aldehyde (0.55 mmol, 1 equiv) and appropriate heterocyclic ring (27C29) (0.73 mmol, 1.3 equiv) were dissolved in ethanol (14 mL) which was followed by the addition of piperidine (90 7.48C7.45 (m, 2H), 7.41C7.37 (m, 2H), 7.32 (d, = 7.8 Hz, 2H), 7.14C7.13 (m, 1H), 6.76 (d, = 8.4 Hz, 1H), 6.54 (s, 1H); 13C NMR (150 MHz, DMSO-178.7, 169.8, 146.0, 145.4, 139.9, 137.1, 129.0, 128.2, 126.7, 123.3, 117.4, 111.6; HRMS-ESI(?) calcd for C16H11N2O3S 311.0490 [M ? H]?, found 311.0505. (Z)-4-((5-Oxo-1-phenyl-2-thioxoimidazolidin-4-ylidene)methyl)-benzoic Acid (32) Prepared from 4-formylbenzoic acid and compound 27 (0.14 g, 0.73 mmol, 1.3 equiv) following the general process B. Yield 78%; mp 300 C; 1H NMR (600 MHz, DMSO-13.07 (s, 1H), 12.70 (s, 1H), 7.96 (d, = 8.4 Hz, 2H), 7.89 (d, = 8.4 Hz, 2H), 7.52C7.46 (m, 3H), 7.38 (d, = 8.4 Hz, 2H), 6.70 (s, 1H); 13C NMR (150 MHz, DMSO-179.6, 167.3, 164.4, 137.2, 133.7, 131.1, 130.6, 129.9, 129.3, 129.2, 111.3; HRMS-ESI(?) calcd for C16H11N2O3S 323.0490 [M ? Moxalactam Sodium H]?, found 323.0490. (Z)-5-(4-Fluorobenzylidene)-3-phenyl-2-thioxoimidazolidin-4-one (33) Prepared from 4-fluorobenzaldehyde and compound 27 (0.14 g, 0.73 mmol, 1.3 equiv) following the general process B. Yield: 74%. 1H NMR.