CAS: 318276-73-2; 6-Fluorocinnoline

📜2-碘-4-氟苯胺置于盐酸,Bis-Triphenylphosphine-Palladium(II) Chloride,Copper(L) Iodide,Potassium Carbonate,三乙胺,Sodium Nitrite体系中,用 四氢呋喃,甲醇,水,邻二氯苯,乙腈 作为反应溶剂,化学反应 10.5H,反应生成 6-氟噌啉
参考文献:Cyclization Of 1-(2-Alkynylphenyl)-3,3-Dialkyltriazenes: A Convenient,High-Yield Synthesis Of Substituted Cinnolines And Isoindazoles
标题:Cyclization Of 1-(2-Alkynylphenyl)-3,3-Dialkyltriazenes: A Convenient,High-Yield Synthesis Of Substituted Cinnolines And Isoindazoles
摘要:A New Route To Isoindazoles And Cinnolines Through The Cyclization Of (2-Alkynylphenyl)Triazenes Under Neutral Conditions Is Presented. The Products That Result From Heating The Starting Triazenes Depend On Both The Type Of Alkyne Ortho To The Triazene Functionality And The Temperature Used. Butadiyne Moieties Ortho To Dialkyltriazenes Yield Bis-Isoindazole Dimers When Heated To 150 Degreesc In Mei. A Requirement For Cyclization In Mei Is That The (2-Alkynylphenyl)Triazene Must Contain A Suitably Electron-Withdrawing Substituent On The Phenyl Ring To Deactivate The Triazene Toward Methylation-Induced Decomposition To An Iodoarene. Ethynyl Moieties Ortho To Dialkyltriazenes Yield Both Isoindazole Dimers As Well As 3-Formylisoindazoles When Subjected To The Same Conditions. Replacing Mei With 1,2-Dichlorobenzene As Solvent Allows For The General Cyclization Of (2-Ethynylphenyl)Dialkyltriazenes. Heating To 170 Degreesc Results In A Mixture Of Isoindazole And Cinnoline Products,Whereas The Cinnolines Are Produced Exclusively In High Yield At 200 Degreesc. Alternatively,The Isoindazoles Can Be Obtained In Good To Excellent Yield By Stirring A 1,2-Dichloroethane Solution Of The Starting Triazene With Cucl Overnight At 50 Degreesc.
DOI:10.1021/jo020229S