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Metal-free propargylation/aza-annulation approach to substituted β-carbolines and evaluation of their photophysical properties

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Abstract

An efficient acid-catalyzed propargylation/aza-annulation sequence was developed under metal-free reaction conditions, thus leading to a one-pot synthesis of a variety of substituted β-carbolines starting from propargylic alcohols and indole 2-carbonyls. This versatile strategy was further extended to the synthesis of 5-azaindoles and 5-azabenzothiazoles. Optical properties suggested that manipulation of electron donor and acceptor moieties on β-carbolines has an impact on their ground and excited state electronic behavior. This leads to blue or green emission and should facilitate the development of organic light emitting diodes (OLEDs). Electrochemical and stability studies revealed that 4a-6 shows ease of redox activity and photostability during illumination.

Graphical abstract: Metal-free propargylation/aza-annulation approach to substituted β-carbolines and evaluation of their photophysical properties

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Publication details

The article was received on 06 Sep 2019, accepted on 08 Oct 2019 and first published on 08 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01959F
Org. Biomol. Chem., 2019, Advance Article

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    Metal-free propargylation/aza-annulation approach to substituted β-carbolines and evaluation of their photophysical properties

    C. R. Reddy, M. Aila, P. Sathish, M. Mrinalini, L. Giribabu, S. Prasanthkumar and R. Grée, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01959F

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