Synthesis and dynamic NMR study of ketenimines derived from tert-butyl isocyanide, alkyl 2-arylamino-2-oxo-acetates, and dialkyl acetylenedicarboxylates

被引：46

作者：

Yavari, Issa ^{[1
]}

Nasiri, Farough ^{[1
]}

Djahaniani, Horieh ^{[1
]}

机构：

[1] Univ Tarbiat Modarres, Dept Chem, Tehran, Iran

来源：

MOLECULAR DIVERSITY | 2004年 / 8卷 / 04期

关键词：

hindered rotation; ketenimines; peri-interaction; tert-butyl isocyanide; three-component reaction; Ugi reaction;

D O I：

10.1023/B:MODI.0000047510.22335.8c

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The adduct produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates was trapped by alkyl 2-arylamino-2-oxo-acetates. When the aryl group is 2-methyl-6-nitrophenyl or 2,6-di-isopropylphenyl, the product exists as two stable rotamers at room temperature as a result of restricted rotation around the Ar-N single bond. When the aryl group is 1-naphthyl or 8-quinolinyl, dynamic NMR effects are observed in the H-1 NMR spectra. The calculated free-energy of activation for interconversion of the rotational isomers in 1-naphthyl and 8-quinolinyl derivatives amounts to about 99 +/- 2 and 68.5 +/- 2 kJ mol(-1), respectively.

引用

页码：431 / 435

页数：5

共 18 条

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[Anonymous], NMR SPECTROSCOPY

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