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Nouvelles voies de synthèse d'hydrazines fonctionnalisées : application à la préparation d'isoniazide monomarqué à l'azote 15 et d'alpha-hydrazinoesters chiraux

Abstract : This work aims at developing a new efficient synthetic route to N-functionalised hydrazine derivatives using N-aminophtalimide, N-acyl and N-alkyloxycarbonylaminophtalimides. The first part describes the synthesis of regioselective singly-labeled nitrogen 15 hydrazide, starting from N-aminophtalimide ([exponent 15]N). The direct application of this first study is the synthesis of two isotopic isomers of isoniazid (a front-line antituberculosis drug), which elucidate the activation of isoniazid by catalase-peroxydase from Mycobacterium tuberculosis. Moreover the reactivity of N-acyl and N-alkyloxycarbonylaminophtalimides which can be considered as hydrazines bearing three electron-withdrawing groups including two incorporated into the phtaloyl moiety, is developed in a second part. These compounds were used in phase transfert catalysis conditions and as acidic partners in the Mitsunobu reaction for the preparation of monoalkylhydrazines, monoalkylhydrazides and alkylcarbazates. In the third part , this current method was extented to include the preparation of protected chiral hydrazinoacid derivatives via the Mistunobu protocol. Finally the conformationel study and reactivity of N-aminophtalimide and its derivatives is reported.
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Theses
File URL :
http://docnum.univ-lorraine.fr/prive/SCD_T_2002_0189_PINTO.pdf
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https://hal.univ-lorraine.fr/tel-01746715
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Submitted on : Thursday, March 29, 2018 - 10:43:11 AM
Last modification on : Friday, February 26, 2021 - 3:02:02 PM

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  • HAL Id : tel-01746715, version 1

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Maria-Fatima Pinto. Nouvelles voies de synthèse d'hydrazines fonctionnalisées : application à la préparation d'isoniazide monomarqué à l'azote 15 et d'alpha-hydrazinoesters chiraux. Autre. Université Henri Poincaré - Nancy 1, 2002. Français. ⟨NNT : 2002NAN10189⟩. ⟨tel-01746715⟩

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