Imidazolidin-4-ones via (3+2) cycloadditions of aza-oxyallyl cations onto (E)-N-arylideneanilines

被引：11

作者：

Eyilcim, Oznur ^{[1
]}

Issever, Sezin ^{[1
]}

Ocal, Nuket ^{[1
]}

Gronert, Scott ^{[2
]}

Erden, Ihsan ^{[3
]}

机构：

[1] Yildiz Tech Univ, Fac Arts & Sci, Dept Chem, Davutpasa Campus, TR-34220 Istanbul, Turkey

[2] Virginia Commonwealth Univ, Dept Chem, 1001 West Main St, Richmond, VA 23284 USA

[3] San Francisco State Univ, Dept Chem & Biochem, 1600 Holloway Ave, San Francisco, CA 94132 USA

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 41期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

Aza-oxyallyl; Aza-cyclopropanone; N-arylimine; (3+2) cycloaddition; Imidazolidin-4-one; ALLENE OXIDE; AZAOXYALLYL CATIONS; SINGLET OXYGEN; INTERMEDIATE; CHEMISTRY; ACCESS;

D O I：

10.1016/j.tetlet.2018.08.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the course of our studies on the chemistry of oxyallyl species we uncovered a new (3+2) cycloaddition of aza-oxyallyl systems, generated in situ from N-benzyloxy-2-chloroamides in the presence of NEt3, onto N-arylimines yielding imidazolidin-4-ones in moderate to good yields. The cycloadditions are regioselective. Computational modeling using DFT at the M062x/6-311+G** level is in support the observed regioselectivities. Although the path to the trans imidazolin-4-one is favored, the cis product is preferred by almost 8 kcal/mol and could be formed by base-catalyzed epimerization. All products were isolated by chromatography and characterized by means of their FTIR, NMR and HRMS data. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3674 / 3677

页数：4

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