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Highly regio- and diastereoselective synthesis of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, based on a post-Ugi condensation: joint experimental and computational study

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Abstract

A novel series of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles were synthesized via a two-step pathway. In the first step, Ugi-four-component condensation of 2-formylindole, amines, (E)-4-alkoxy-4-oxobut-2-enoic acids, and isocyanides gave the corresponding Ugi-adducts. This adduct underwent intramolecular hydroamination in the presence of K2CO3 in CH3CN at room temperature to afford diastereoselective synthesis of a range of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles. A comparison of experimentally observed CD and UV–visible spectra with the theoretical DFT calculated ECD spectra was used to predict the major diastereomer.

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Acknowledgements

The authors would like to thank the Alzahra University and Iran National Science Foundation (INSF) for financial support. We are also very grateful for Prof. Adolf Gogoll and Dr. Sandra Olsson from Uppsala University (Uppsala, Sweden) for doing experimental ECD and UV–visible spectroscopy.

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Authors and Affiliations

  1. Department of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran

    Morteza Shiri, Majid M. Heravi, Vahideh Zadsirjan & Mina Ghiasi

  2. School of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, South Africa

    Suhas A. Shintre, Neil A. Koorbanally & Thishana Singh

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  1. Morteza Shiri
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Correspondence to Morteza Shiri or Majid M. Heravi.

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Shiri, M., Heravi, M.M., Zadsirjan, V. et al. Highly regio- and diastereoselective synthesis of oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, based on a post-Ugi condensation: joint experimental and computational study. J IRAN CHEM SOC 16, 1517–1526 (2019). https://doi.org/10.1007/s13738-019-01632-3

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