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.
Original language | English (US) |
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Pages (from-to) | 169-173 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 55 |
Issue number | 1 |
DOIs | |
State | Published - Jan 1 2014 |
Externally published | Yes |
Keywords
- 7-Azaindoles
- Di-7-azaindolylmethanes
- MAOS
- Microwave
- One-pot reactions
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry