Simple and efficient approaches to the synthesis of fluorinated benzoazaheterocycles with good yields are reported. Firstly a series of polyfluorinated 2-alkynylanilines – the versatile building blocks – was synthesized by the Sonogashira reaction of o-iodoaniline with terminal alkynes. Then the transformations of the obtained 2,3,4-trifluo-6-alkynilanilines in the presence of KOH or PdCl₂ in MeCN, and in the presence of monohydrate of p-toluenesulfonic acid (p-TSA•H₂O) in MeOH, EtOH or benzene were investigated. It was found that Ph- and n-Bu-containing alkynylanilines by action of PdCl₂ in MeCN underwent an intramolecular cyclization reaction to produce the corresponding indoles in high yields. The reaction of KOH with alkynes containing the tertiary alcohol function at the triple bond produced the unsubstituted on the pyrrole ring indole. It was found that fluorinated 2-alkynilanilines can be transformated into indoles, 2-arylketones and 2,3-dihydroquinolines by action of p-TSA•H₂O in boiling alcohols, depending on the substituent at the triple bond. The use of benzene as a solvent in the reaction of p-TSA•H₂O with polyfluorinated alkynes, bearing an alcohol group resulted in representative series of 2,3-dihydroquinolinones containing a substituents R¹ and R² in the 2nd position of their structure (R = H, H; Me, Me; H, i-Pr; H, Ph).

据报道，简单有效的方法合成氟化苯并氮杂杂环具有良好的收率。首先，通过邻碘苯胺的Sonogashira反应与末端炔烃合成了一系列多氟2-炔基苯胺（通用的构建单元）。然后在MeCN中存在KOH或PdCl ₂的情况下，在对甲苯磺酸一水合物（p -TSA•H ₂ O）在MeOH中的存在下，转化获得的2,3,4-三氟-6-炔基苯胺，乙醇或苯进行了研究。发现通过PdCl ₂的作用，含Ph和n -Bu的炔基苯胺MeCN中的Indol进行了分子内环化反应，以高产率生产相应的吲哚。KOH与在三键处含有叔醇官能团的炔烃的反应在吡咯环吲哚上产生未取代的基团。已经发现，在沸腾的醇中，取决于三键上的取代基，氟化的2-炔基苯胺可以通过对-TSA•H ₂ O的作用转化为吲哚，2-芳基酮和2,3-二氢喹啉。使用苯作为溶剂在p -TSA•H ₂ O与带有醇基的多氟炔烃反应中，得到具有代表性的2，3-二氢喹啉酮系列，其取代基为R ¹和R ²在其结构的第二位置（R = H，H； Me，Me； H，i- Pr； H，Ph）。