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N-芳基-2-乙烯基氮杂环丙烷重排为苯并氮杂䓬和二氢吡咯:一项合成与理论研究。

Rearrangement of N-aryl-2-vinylaziridines to benzoazepines and dihydropyrroles: a synthetic and theoretical study.

作者信息

Fantauzzi Simone, Gallo Emma, Caselli Alessandro, Piangiolino Cristiana, Ragaini Fabio, Re Nazzareno, Cenini Sergio

机构信息

Dipartimento di Chimica Inorganica, Metallorganica e Analitica Lamberto Malatesta, Università degli Studi di Milano and ISTM-CNR, Via Venezian 21, I-20133 Milano, Italy.

出版信息

Chemistry. 2009;15(5):1241-51. doi: 10.1002/chem.200801148.

DOI:10.1002/chem.200801148
PMID:19072944
Abstract

Herein we report the one-pot synthesis of several N-heterocyclic compounds by rearrangement reactions of N-aryl-2-vinylaziridines. The optimization of the synthetic methodology employed allowed us to obtain differently substituted 2,5-dihydro-1H-benzo[b]azepines in good yields and purities. The relationship between the nature of the starting N-aryl-2-vinylaziridine and the obtained N-heterocycle was also investigated. Finally, to rationalize all the experimental results reported in this paper a theoretical study was performed that casts light on the reaction mechanism.

摘要

在此,我们报道了通过N-芳基-2-乙烯基氮丙啶的重排反应一锅法合成几种氮杂环化合物。所采用的合成方法的优化使我们能够以良好的产率和纯度获得不同取代的2,5-二氢-1H-苯并[b]氮杂䓬。还研究了起始N-芳基-2-乙烯基氮丙啶的性质与所得氮杂环之间的关系。最后,为了阐明本文报道的所有实验结果,进行了一项理论研究,该研究揭示了反应机理。

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