880094-83-7 (5-溴-3,4-二氢喹啉-2(1H)-酮,5-bromo-3,4-dihydro-1H-quinolin-2-one)

反应条件：

1.1 Reagents: Potassium carbonate , Tempo , Sodium iodide , Oxygen Catalysts: Water Solvents: Dimethylformamide ; 8 h, rt

参考文献：

Selective electrochemical oxidation of tetrahydroquinolines to 3,4-dihydroquinolones

Tan, Yu-Fang; et al, Green Chemistry, 2022, 24(11), 4581-4587

合成路线：1 步

2247446-52-0

_50%

反应条件：

1.1 Catalysts: Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate , Chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl](8-quinolinol… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 12 h, 60 °C

参考文献：

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Hong, Seung Youn ; et al, Science (Washington, 2018, 359(6379), 1016-1021

合成路线：1 步

2247446-52-0

_42%

反应条件：

1.1 Reagents: Silver carbonate , Sodium tetrafluoroborate Catalysts: 8-Hydroxyquinoline , Carbonyldiiodo[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]cobal… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 3 h, rt

参考文献：

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)-H Amidation

Tian, Xun ; et al, Advanced Synthesis & Catalysis, 2021, 363(4), 1050-1058

合成路线：1 步

1228680-87-2

_27%

反应条件：

1.1 30 min, 160 - 165 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：2 步

1228680-87-2

530-62-1

反应条件：

1.1 Solvents: Dichloromethane ; 5 - 60 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; rt
2.1 Reagents: Silver carbonate , Sodium tetrafluoroborate Catalysts: 8-Hydroxyquinoline , Carbonyldiiodo[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]cobal… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 3 h, rt

参考文献：

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)-H Amidation

Tian, Xun ; et al, Advanced Synthesis & Catalysis, 2021, 363(4), 1050-1058

合成路线：2 步

1228680-87-2

530-62-1

反应条件：

1.1 Solvents: Dichloromethane ; 30 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Catalysts: Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate , Chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl](8-quinolinol… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 12 h, 60 °C

参考文献：

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Hong, Seung Youn ; et al, Science (Washington, 2018, 359(6379), 1016-1021

合成路线：2 步

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; 4 h, reflux
1.2 Reagents: Sodium methoxide , Hydroxyamine hydrochloride Solvents: Methanol ; 6.5 h, reflux
2.1 30 min, 160 - 165 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：3 步

反应条件：

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Tetrahydrofuran ; 1 h, rt
1.2 Reagents: Hydroxyamine hydrochloride ; overnight, rt
2.1 Solvents: Dichloromethane ; 5 - 60 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; rt
3.1 Reagents: Silver carbonate , Sodium tetrafluoroborate Catalysts: 8-Hydroxyquinoline , Carbonyldiiodo[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]cobal… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 3 h, rt

参考文献：

Room Temperature Benzofused Lactam Synthesis Enabled by Cobalt(III)-Catalyzed C(sp2)-H Amidation

Tian, Xun ; et al, Advanced Synthesis & Catalysis, 2021, 363(4), 1050-1058

合成路线：3 步

反应条件：

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Tetrahydrofuran ; 1 h, rt
1.2 Reagents: Hydroxyamine hydrochloride ; 16 h, rt
2.1 Solvents: Dichloromethane ; 30 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water
3.1 Catalysts: Sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate , Chloro[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl](8-quinolinol… Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 12 h, 60 °C

参考文献：

Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts

Hong, Seung Youn ; et al, Science (Washington, 2018, 359(6379), 1016-1021

合成路线：3 步

7345-79-1

反应条件：

1.1 Reagents: Phosphorus , Hydrogen iodide Solvents: Water ; 1.25 h, reflux
2.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; 4 h, reflux
2.2 Reagents: Sodium methoxide , Hydroxyamine hydrochloride Solvents: Methanol ; 6.5 h, reflux
3.1 30 min, 160 - 165 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：4 步

6630-33-7

141-82-2

反应条件：

1.1 -
2.1 Reagents: Phosphorus , Hydrogen iodide Solvents: Water ; 1.25 h, reflux
3.1 Reagents: Sulfuric acid Solvents: Methanol , Water ; 4 h, reflux
3.2 Reagents: Sodium methoxide , Hydroxyamine hydrochloride Solvents: Methanol ; 6.5 h, reflux
4.1 30 min, 160 - 165 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：1 步

15115-60-3

_72%

反应条件：

1.1 Reagents: Sodium azide ; 1.5 min, 130 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：1 步

500566-21-2

_50%

1228678-45-2

反应条件：

1.1 1.5 h, 115 - 120 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：1 步

2750345-37-8

_43%

反应条件：

1.1 Catalysts: Tris[2-(2-pyridinyl-κN)-5-(trifluoromethyl)phenyl-κC]iridium Solvents: Acetonitrile ; 12 h, 25 °C

参考文献：

Visible-Light Induced C(sp2)-H Amidation with an Aryl-Alkyl σ-Bond Relocation via Redox-Neutral Radical-Polar Crossover

Keum, Hyeyun ; et al, Angewandte Chemie, 2021, 60(48), 25235-25240

合成路线：1 步

2247446-52-0

_27%

反应条件：

1.1 Reagents: Silica Catalysts: Ferric bromide ; 1 h, rt

参考文献：

Iron-Catalyzed Intramolecular Arene C(sp2)-H Amidations under Mechanochemical Conditions

Shi, Peng; et al, Angewandte Chemie, 2022, 61(30),

合成路线：2 步

1228679-07-9

1228678-45-2

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol ; 4 h, reflux
1.2 Reagents: Sodium methoxide , Hydroxyamine hydrochloride Solvents: Methanol ; 6.5 h, reflux
2.1 1.5 h, 115 - 120 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：2 步

反应条件：

1.1 Solvents: Dichloromethane ; 30 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Silica Catalysts: Ferric bromide ; 1 h, rt

参考文献：

Iron-Catalyzed Intramolecular Arene C(sp2)-H Amidations under Mechanochemical Conditions

Shi, Peng; et al, Angewandte Chemie, 2022, 61(30),

合成路线：2 步

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Diethyl ether ; 0 °C; 0 °C → rt; 12 h, rt
2.1 Catalysts: Tris[2-(2-pyridinyl-κN)-5-(trifluoromethyl)phenyl-κC]iridium Solvents: Acetonitrile ; 12 h, 25 °C

参考文献：

Visible-Light Induced C(sp2)-H Amidation with an Aryl-Alkyl σ-Bond Relocation via Redox-Neutral Radical-Polar Crossover

Keum, Hyeyun ; et al, Angewandte Chemie, 2021, 60(48), 25235-25240

合成路线：2 步

反应条件：

1.1 -
2.1 Reagents: Sodium azide ; 1.5 min, 130 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：3 步

反应条件：

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Tetrahydrofuran ; 1 - 2 h, rt
1.2 Reagents: Hydroxyamine hydrochloride Solvents: Dichloromethane ; overnight, rt
2.1 Solvents: Dichloromethane ; 30 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water
3.1 Reagents: Silica Catalysts: Ferric bromide ; 1 h, rt

参考文献：

Iron-Catalyzed Intramolecular Arene C(sp2)-H Amidations under Mechanochemical Conditions

Shi, Peng; et al, Angewandte Chemie, 2022, 61(30),

合成路线：3 步

1228678-40-7

1228678-45-2

反应条件：

1.1 -
2.1 Reagents: Sulfuric acid Solvents: Methanol ; 4 h, reflux
2.2 Reagents: Sodium methoxide , Hydroxyamine hydrochloride Solvents: Methanol ; 6.5 h, reflux
3.1 1.5 h, 115 - 120 °C

参考文献：

Reactions of hydroxylamine derivatives in polyphosphoric acid

Padegimas, Stanley J., 1970, , ,

合成路线：3 步

7345-79-1