title: Microwave-assisted, one-pot reaction of 7-azaindoles and aldehydes: a facile route to novel di-7-azaindolylmethanes.
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 towards 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.
authors.affiliation: Department of Radiology and Radiological Sciences, Vanderbilt University Medical Center, Nashville, TN 37232, USA ; Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Md Imam
authors.initials: MI
authors.lastname: Uddin
authors.affiliation: Department of Radiology and Radiological Sciences, Vanderbilt University Medical Center, Nashville, TN 37232, USA ; Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Jason R
authors.initials: JR
authors.lastname: Buck
authors.affiliation: Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Michael L
authors.initials: ML
authors.lastname: Schulte
authors.affiliation: Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Dewei
authors.initials: D
authors.lastname: Tang
authors.affiliation: Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Samir A
authors.initials: SA
authors.lastname: Saleh
authors.affiliation: Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA.
authors.forename: Yiu-Yin
authors.initials: YY
authors.lastname: Cheung
authors.affiliation: Department of Biochemistry and Center for Structural Biology, Vanderbilt University, Nashville, TN 37232, USA.
authors.forename: Joel
authors.initials: J
authors.lastname: Harp
authors.affiliation: Department of Radiology and Radiological Sciences, Vanderbilt University Medical Center, Nashville, TN 37232, USA ; Vanderbilt University Institute of Imaging Science, Vanderbilt University, Nashville, TN 37232-2310, USA ; Department of Biomedical Engineering, Vanderbilt University, Nashville, TN 37232, USA ; Vanderbilt Ingram Cancer Center, Vanderbilt University Medical Center, Nashville, TN 37232, USA ; Program in Chemical and Physical Biology, Vanderbilt University School of Medicine, Nashville, TN 37232, USA ; Department of Neurosurgery, Vanderbilt University Medical Center, Nashville, TN 37232, USA.
authors.forename: H Charles
authors.initials: HC
authors.lastname: Manning
keywords: 7-Azaindoles; Di-7-azaindolylmethanes; MAOS; Microwave; One-pot; reactions