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通过[2 + 3]环加成反应合成功能化二氢-1Η-吡咯嗪和螺吡咯嗪。

A synthesis of functionalized dihydro-1Η-pyrrolizines and spiropyrrolizines via [2 + 3] cycloaddition reactions.

作者信息

Yavari Issa, Baoosi Leila, Halvagar Mohammad R

机构信息

Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.

Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.

出版信息

Mol Divers. 2017 May;21(2):265-271. doi: 10.1007/s11030-017-9725-z. Epub 2017 Feb 12.

Abstract

A one-pot synthesis of dihydro-1H-pyrrolizine derivatives via [Formula: see text] cycloaddition reaction of azomethine ylides, prepared in situ from proline and ninhydrin, with dialkyl acetylenedicarboxylates, in alcohols, is described. When sarcosine was used instead of proline, functionalized spiropyrrolizines were obtained. Under these conditions, alkyl propiolates produced stable spirans.

摘要

描述了一种在醇中,通过脯氨酸和茚三酮原位制备的甲亚胺叶立德与二烷基乙炔二羧酸酯发生[公式:见原文]环加成反应一锅法合成二氢-1H-吡咯嗪衍生物的方法。当用肌氨酸代替脯氨酸时,可得到功能化的螺吡咯嗪。在这些条件下,丙酸炔丙酯生成稳定的螺环化合物。

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