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Water‐Facilitated Nitromethane‐Mediated Cyclization of 2‐(Phenylvinyl)benzhydrols: Access to 1,3‐Diphenyl‐1H‐indenes with Antitumor Activity

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Hauguel, Camille | Tran, Christine | Provot, Olivier | Bignon, Jérôme | Gandon, Vincent | Hamze, Abdallah

Edité par CCSD ; Wiley-VCH Verlag -

International audience. Abstract This work reports a mild and operationally accessible method for synthesizing 1,3‐diphenyl‐1H‐indene derivatives from N ‐tosylhydrazones and bromobenzhydrols as readily available reactants. Moreover, the cyclization step does not require metal catalysis, the addition of an acid, or a very high temperature. We report a combined experimental and computational study on the mechanism of this cyclization. In addition, we demonstrate the utility of this methodology by synthesizing a large number of products, even on the gram‐scale, and by the obtention of new biologically relevant molecules. magnified image

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