Microwave-assisted,one-pot reaction of 7-azaindoles and aldehydes: a facile route to novel di-7-azaindolylmethanes |
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| Authors: | Md Imam Uddin Jason R Buck Michael L Schulte Dewei Tang Samir A Saleh Yiu-Yin Cheung Joel Harp H Charles Manning |
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| Institution: | 1. Department of Radiology and Radiological Sciences, Vanderbilt University Medical Center, Nashville, TN 37232, USA;2. Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232, USA;3. Department of Biomedical Engineering, Vanderbilt University, Nashville, TN 37232, USA;4. Vanderbilt Ingram Cancer Center, Vanderbilt University Medical Center, Nashville, TN 37232, USA;5. Program in Chemical and Physical Biology, Vanderbilt University School of Medicine, Nashville, TN 37232, USA;6. Department of Neurosurgery, Vanderbilt University Medical Center, Nashville, TN 37232, USA;g Department of Biochemistry and Center for Structural Biology, Vanderbilt University, Nashville, TN 37232, USA |
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| 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. |
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| Keywords: | Microwave 7-Azaindoles Di-7-azaindolylmethanes One-pot reactions MAOS |
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