Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5271339 | Tetrahedron Letters | 2014 | 5 Pages |
Abstract
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.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Md. Imam Uddin, Jason R. Buck, Michael L. Schulte, Dewei Tang, Samir A. Saleh, Yiu-Yin Cheung, Joel Harp, H. Charles Manning,