1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 4 h / -20 - 0 °C / |Inert atmosphere 2.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 3.1: triethylamine; triphenylphosphine; palladium diacetate / toluene / 3.33 h / 25 - 110 °C / |Inert atmosphere 4.1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 24 h / 25 °C / |Inert atmosphere; |UV-irradiation 5.1: thiourea / methanol / 2 h / 25 °C / |Inert atmosphere 6.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 7.1: toluene / 3 h / 110 °C / |Inert atmosphere 8.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 9.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 10.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 10.2: pH 3 11.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 12.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 13.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 14.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 2.1: triethylamine; triphenylphosphine; palladium diacetate / toluene / 3.33 h / 25 - 110 °C / |Inert atmosphere 3.1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 24 h / 25 °C / |Inert atmosphere; |UV-irradiation 4.1: thiourea / methanol / 2 h / 25 °C / |Inert atmosphere 5.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 6.1: toluene / 3 h / 110 °C / |Inert atmosphere 7.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 8.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 9.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 9.2: pH 3 10.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 11.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 12.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 13.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 2: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 3: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 4: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: triethylamine; triphenylphosphine; palladium diacetate / toluene / 3.33 h / 25 - 110 °C / |Inert atmosphere 2.1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 24 h / 25 °C / |Inert atmosphere; |UV-irradiation 3.1: thiourea / methanol / 2 h / 25 °C / |Inert atmosphere 4.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 5.1: toluene / 3 h / 110 °C / |Inert atmosphere 6.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 7.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 8.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 8.2: pH 3 9.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 10.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 11.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 12.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: 5,15,10,20-tetraphenylporphyrin; oxygen / dichloromethane / 24 h / 25 °C / |Inert atmosphere; |UV-irradiation 2.1: thiourea / methanol / 2 h / 25 °C / |Inert atmosphere 3.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 4.1: toluene / 3 h / 110 °C / |Inert atmosphere 5.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 6.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 7.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 7.2: pH 3 8.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 9.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 10.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 11.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: thiourea / methanol / 2 h / 25 °C / |Inert atmosphere 2.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 3.1: toluene / 3 h / 110 °C / |Inert atmosphere 4.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 5.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 6.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 6.2: pH 3 7.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 8.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 9.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 10.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: triethylamine / dichloromethane / 1.5 h / 0 °C / |Inert atmosphere 2.1: toluene / 3 h / 110 °C / |Inert atmosphere 3.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 4.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 5.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 5.2: pH 3 6.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 7.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 8.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 9.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: toluene / 3 h / 110 °C / |Inert atmosphere 2.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 3.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 4.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 4.2: pH 3 5.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 6.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 7.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 8.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: phosphorous acid trimethyl ester / 16 h / 111 °C / |Inert atmosphere 2.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 3.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 3.2: pH 3 4.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 5.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 6.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 7.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme

1.1: hydrogenchloride / dichloromethane; diethyl ether / 0.25 h / 0 °C / |Inert atmosphere 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 5 h / 0 - 25 °C 2.2: pH 3 3.1: N-ethyl-N,N-diisopropylamine; 1-hydroxy-7-aza-benzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 4.1: dichloromethane / 3 h / 0 - 25 °C / |Inert atmosphere 5.1: triethylamine / dichloromethane / 15 h / 0 - 25 °C / |Inert atmosphere 6.1: lithium hexamethyldisilazane; sulfur / tetrahydrofuran / 2.08 h / 25 °C / |Inert atmosphere View Scheme