1364232-72-3Relevant academic research and scientific papers
Intramolecular ipso -halocyclization of 4-(p -unsubstituted-aryl)-1-alkynes leading to spiro[4,5]trienones: Scope, application, and mechanistic investigations
Tang, Bo-Xiao,Zhang, Yue-Hua,Song, Ren-Jie,Tang, Dong-Jun,Deng, Guo-Bo,Wang, Zhi-Qiang,Xie, Ye-Xiang,Xia, Yuan-Zhi,Li, Jin-Heng
experimental part, p. 2837 - 2849 (2012/05/05)
A new, general method for the synthesis of spiro[4,5]trienones is described by the intramolecular ipso-halocyclization of 4-(p-unsubstituted-aryl)-1- alkynes. In the presence of halide electrophiles, a variety of 4-(p-unsubstituted-aryl)-1-alkynes underwent the intramolecular ipso-halocyclization with water smoothly, affording the corresponding halo-substituted spiro[4,5]trienones in moderate to good yields. The obtained spiro[4,5]trienones can be applied in constructing the azaquaternary tricyclic skeleton via Pd-catalyzed Heck reaction. Notably, the prepared spiro[4,5]trienones and azaquaternary tricycles are of importance in the areas of pharmaceuticals and agrochemicals. The mechanism of the intramolecular ipso-halocyclization reaction is also discussed according to the 18O-labeling experiments and DFT calculations.
