1522362-10-2Relevant academic research and scientific papers
Microwave-assisted, one-pot reaction of 7-azaindoles and aldehydes: A facile route to novel di-7-azaindolylmethanes
Uddin, Md. Imam,Buck, Jason R.,Schulte, Michael L.,Tang, Dewei,Saleh, Samir A.,Cheung, Yiu-Yin,Harp, Joel,Manning, H. Charles
supporting information, p. 169 - 173 (2014/01/06)
A novel and highly efficient synthetic method leveraging microwave-assisted organic synthesis (MAOS) to yield di-7-azaindolylmethanes (DAIMs) is reported. Under MAOS conditions, reaction of 7-azaindole with aldehydes resulted predominantly in DAIMs, as opposed to the expected 7-azaindole addition products that form at ambient temperature. Based upon studies of different indoles and azaindoles with various aromatic and aliphatic aldehydes, we herein propose a mechanism where rapid and efficient microwave heating promotes nucleophilicity of 7-azaindoles toward the corresponding alkylidene-azaindolene intermediate to form the DAIM. This sequence provides a versatile approach to efficiently synthesize novel DAIMs that may be useful pharmaceuticals.
