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Synthesis of Five-, Six- and Seven-Membered Hetero Ring Annulated Imidazo[4,5-b] carbazoles and Azacarbazoles of Medicinal Interest

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Chemistry for Sustainable Development

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Abstract

Application of Japp-Klingemann reaction with benzimidazolyl diazonium chloride (4) on 2-hydroxymethylidene cyclohexanone (6a) and N-benzyl-3-hydroxymethylidene-4-piperidone (6b) yielded the corresponding hydrazones (7a-b) which underwent facile Fischer-indolization in acid to give the imidazo condensed oxocarbazole and imidazo condensed oxoazacarbazoles (8a-b). Subsequent treatment of (8a-b) with (i) HCOOEt, NaOEt (ii) C6H5CHO (iii) CS2, CH3I, NaOEt and (iv) Me2NCH(OMe)2 yielded in succession the corresponding enolic ethers (9a-b), dimethylaminomethylene ketones (10a-b), oxoketenedithioacetals (11a-b) and □,□-unsaturated ketones (12a-b) respectively. Interaction of (9a-b), (10a-b), (11a-b) and (12a-b) with bidentate nucleophiles such as hydroxylamine hydrochloride and hydrazine hydrate afforded the corresponding isoxazolo and pyrazolo incorporated derivatives of imidazo condensed carbazoles and azacarbazoles (13a-l). Similar interaction with urea and thiourea yielded corresponding pyrimido incorporated imidazo condensed carbazoles and azacarbazoles (14a-r). Reactions of these intermediates with o-phenylenediamine, o-aminophenol and o-aminothiophenol produced benzodiazepino, benzoxazepino and benzothiazepino incorporated imidazo condensed carbazoles and azacarbazoles (15a-r) respectively. Structures of all the compounds have been unequivocally established on the basis of their elemental and spectral data. Antifungal and antibacterial activities of some of the synthesized compounds have been carried out.

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Acknowledgement

Authors are thankful to CURIE (Consolidation of University Research for Innovation and Excellence in Women’s University) programme of the Department of Science and Technology (DST), Government of India for funding.

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Authors and Affiliations

  1. Department of Chemistry, Banasthali University, Banasthali, Rajasthan, 304022, India

    Bhawani Singh, Bharti Vashishtha & D. Kishore

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  1. Bhawani Singh
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  2. Bharti Vashishtha
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  3. D. Kishore
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Correspondence to Bhawani Singh .

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Editors and Affiliations

  1. Faculty of Science, Dept. Chemistry, University of Mauritius, Reduit, Mauritius

    Minu Gupta Bhowon

  2. Faculty of Science, Dept. Chemistry, University of Mauritius, Reduit, Mauritius

    Sabina Jhaumeer-Laulloo

  3. Faculty of Science, Dept. Chemistry, University of Mauritius, Reduit, Mauritius

    Henri Li Kam Wah

  4. Faculty of Science, Dept. Chemistry, University of Mauritius, Reduit, Mauritius

    Ponnadurai Ramasami

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Singh, B., Vashishtha, B., Kishore, D. (2012). Synthesis of Five-, Six- and Seven-Membered Hetero Ring Annulated Imidazo[4,5-b] carbazoles and Azacarbazoles of Medicinal Interest. In: Gupta Bhowon, M., Jhaumeer-Laulloo, S., Li Kam Wah, H., Ramasami, P. (eds) Chemistry for Sustainable Development. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-8650-1_30

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