1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.75 h / 120 °C 2: 2.) Et3N / 1.) RT, 20 h, 2.) ethyl acetate, RT, 1 h 3: 90 percent / N-benzylacridinium bromide / acetonitrile / Ambient temperature 4: H2 / Pd / 760 Torr 5: NaOEt / ethanol / 0.5 h / Heating View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SOCl2 / 2 h / Ambient temperature 9: 70 percent / 0.25 h / 100 °C View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SOCl2 / 2 h / Ambient temperature 9: 60 percent / acetonitrile / 0.5 h / Heating View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SnCl4 / acetonitrile / 2 h / Ambient temperature 9: 86 percent / CH3OH, NaOMe / tetrahydrofuran / Ambient temperature View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SOCl2 / 2 h / Ambient temperature 9: 60 percent / acetonitrile / 0.5 h / Heating 10: 60 percent / SOCl2 / 20 h / Ambient temperature View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 65 percent / n-BuLi / tetrahydrofuran / 3 h / 0 - 10 °C 6: 58 percent / CH2Cl2 / 1 h / Ambient temperature 7: 77 percent / KOH / H2O; ethane-1,2-diol / 160 - 170 °C 8: SOCl2 / 2 h / Ambient temperature View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 2.) 50percent aq KOH / 1.) THF, 20 deg C, 3 h and reflux, 5 min, 2.) ethylene glycol, 160 deg C, 15 min View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 25 percent / 50percent aq KOH / tetrahydrofuran; ethane-1,2-diol / 1.) THF, 20 deg C, 3 h and reflux, 5 min, 2.) ethylene glycol, 160 deg C, 15 min View Scheme

1: 55 percent / tetrahydrothiophene 1,1-dioxide / 0.5 h / 120 °C 2: 2.) Et3N / 1.) CH3Cl, r.t.; 2.) EtOAc, r.t. 3: 90 percent / N-benzyl acridinium bromide / acetonitrile / 1 h / Ambient temperature 4: 80 percent / H2, NaHCO3 / 10percent Pd-C / ethanol / 5 h / 760 Torr 5: 44 percent / 50percent aq KOH / tetrahydrofuran; ethane-1,2-diol / 1.) THF, 20 deg C, 3 h and reflux, 5 min, 2.) ethylene glycol, 160 deg C, 15 min View Scheme