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    The Hemetsberger reaction: A new approach to the synthesis of novel dihydroindoloindole systems
    (Arkat Usa Inc, 2020) Bingül, Murat; Kumar, Naresh; Black, David StC
    The Hemetsberger indole synthesis provides an alternative method for the preparation of dihydroindoloindole systems. Two novel examples, dimethyl 3,8-dihydroindolo[7,6-g]indole-2,7-dicarboxylate and dimethyl 1,6dihydroindolo[5,4-e]indole- 2,7-dicarboxylate, were succesfully prepared by the Hemetsberger indole sythesis. The ester functionality on the C-2 position was used for the further elaboration of these tetracyclic systems.
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    Synthesis and reactions of new 2-hydroxymethyldimethoxyindoles
    (Pergamon-Elsevier Science Ltd, 2016) Bingul, Murat; Kumar, Naresh; Black, David StC
    Lithium aluminium hyride was used as a reducing agent to prepare a range of 2-hydroxymethyldimethoxyindole derivatives from the related methyl esters. Acid-catalysed reactions of these indole-2-methanols yielded indolo-cyclotriveratrylenes linked through C-2 and C-3. The related indole-2-carbaldehydes were prepared via oxidation of the indole-2-methanols in the presence of manganese dioxide. Vilsmeier formylation was explored to prepare new formylated indole-2-carbaldehydes. Furthermore, the treatment of indole-2-carbaldehydes with nitromethane led to the formation of 2-nitrovinylindoles. (C) 2015 Elsevier Ltd. All rights reserved.
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    Synthesis, reactivity and biological properties of methoxy-activated indoles
    (Society Chimica Italiana, 2021) Şengül, İbrahim F.; Bingül, Murat; Kandemir, Hakan; Kumar, Naresh; Black, David StC.; Attanasi, O.A.; Gabriele, B.; Merino, P.; Spinelli, D.
    Indoles continue to play a central role in the development of new structures of chemical and biological interest. They are the source of numerous biologically active natural products by virtue of their derivation from tryptophan units which are essential to peptide, protein and enzyme structures. Although the indole unit is electron rich and displays a wide range of reactivity, many naturally-occurring indoles contain methoxy substituents, which enhance their reactivity. The synthesis of methoxyindoles has also become a strategy for diversifying the regiochemical behaviour of indoles. This review brings together a wide range of information relating to indoles incorporating one, two, or three methoxy groups. It deals with aspects of synthesis, reactivity, and biological activity as well as summarizing the scope of important natural products.