A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation

作者：Joy M Nibin; Bodke Yadav D^*; Khader K K Abdul; Padusha M Syed Ali; Sajith Ayyiliyath M; Muralidharan A

来源：RSC Advances, 2014, 4(38): 19766-19777.

DOI：10.1039/c4ra01720j

A facile, efficient and reliable access for the synthesis of an array of 4-methyl- 7-(alkyl/aryl/heteroaryl) amino and amido coumarins has been developed by treating 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with various amines and pyridones in presence of a catalyst combination of Pd-2(dba)(3)/xantphos under microwave irradiation. Nonaflates coupled efficiently to give the diaryl amines in acceptable to excellent yields whereas the corresponding triflate was unstable, yielding the detriflated product as well as the hydrolyzed product as competing side products along with the desired product. The wide bite angle (108 degrees) of xantphos, employment of Cs2CO3 as a mild base and the utilization of TBAF center dot 3H(2)O as an additive proved to be key for success of the reaction.

• 出版日期2014