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2-Amino-5-Bromo-3-Iodoacetophenone and 2-Amino-5-Bromo-3-Iodobenzamide as Synthons for Novel Polycarbo-Substituted Indoles and Their Annulated Derivatives

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Emerging Trends in Chemical Sciences (ICPAC 2016)

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Abstract

2-Amino-5-bromo-3-iodoacetophenone and 2-amino-5-bromo-3-iodobenzamide represent important synthons for the design and synthesis of various nitrogen-containing heterocyclic compounds and their annulated derivatives. We have demonstrated that these halogenated aniline derivatives undergo palladium catalyzed Sonogashira cross-coupling with terminal acetylenes to afford the corresponding 2-amino-3-(arylalkynyl)acetophenones and 2-amino-3-(arylalkynyl)benzamides. These alkynylated aniline derivatives in which the alkynyl moiety is adjacent to the nucleophilic nitrogen atom were, in turn, subjected to palladium chloride-mediated heteroannulation to yield novel 1-(2-aryl-1H-indol-7-yl)ethanones and 2-aryl-1H-indole-7-carboxamides, respectively. Molecular hybridization to append an indole moiety to a chalcone framework was achieved via initial Claisen-Schmidt aldol condensation of 2-amino-5-bromo-3-iodoacetophenone with benzaldehyde derivatives followed by sequential palladium catalyzed Sonogashira cross-coupling and heteroannulation. Likewise, boric acid-mediated cyclocondensation of the 3-alkynyl-5-bromoanthranilamides with benzaldehyde derivatives followed by palladium chloride-mediated cyclization afforded the corresponding 2,3-dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones.

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Acknowledgements

The authors are grateful to the University of South Africa and the National Research Foundation (SA) for financial assistance.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria, 0003, South Africa

    Mmakwena M. Mmonwa & Malose J. Mphahlele

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  1. Mmakwena M. Mmonwa
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  2. Malose J. Mphahlele
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Corresponding author

Correspondence to Malose J. Mphahlele .

Editor information

Editors and Affiliations

  1. Dept. of Chem., Fac. of Science, University of Mauritius, Reduit, Mauritius

    Ponnadurai Ramasami

  2. Dept. of Chem., Fac. of Science, University of Mauritius, Reduit, Mauritius

    Minu Gupta Bhowon

  3. Dept. of Chem., Fac. of Science, University of Mauritius, Reduit, Mauritius

    Sabina Jhaumeer Laulloo

  4. Dept. of Chem., Fac. of Science, University of Mauritius, Reduit, Mauritius

    Henri Li Kam Wah

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Mmonwa, M.M., Mphahlele, M.J. (2018). 2-Amino-5-Bromo-3-Iodoacetophenone and 2-Amino-5-Bromo-3-Iodobenzamide as Synthons for Novel Polycarbo-Substituted Indoles and Their Annulated Derivatives. In: Ramasami, P., Gupta Bhowon, M., Jhaumeer Laulloo, S., Li Kam Wah, H. (eds) Emerging Trends in Chemical Sciences. ICPAC 2016. Springer, Cham. https://doi.org/10.1007/978-3-319-60408-4_23

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