A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones,Organic Chemistry Frontiers

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A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-11-01 00:00:00 , DOI: 10.1039/c7qo00888k
A. S. Filatov _{1,

2,

3} , N. A. Knyazev _{2,

2,

3,

4,

5} , M. N. Ryazantsev _{1,

2,

2,

3,

4} , V. V. Suslonov _{1,

2,

3} , A. G. Larina _{1,

2,

3} , A. P. Molchanov _{1,

2,

3} , R. R. Kostikov _{1,

2,

3} , V. M. Boitsov _{2,

3,

4,

6,

7} , A. V. Stepakov _{1,

2,

3,

8,

9}

Affiliation

A simple and efficient method has been developed for the synthesis of complex compounds with spiro-fused 11H-indeno[1,2-b]quinoxaline and cyclopropa[a]pyrrolizine or azabicyclo[3.1.0]hexane moieties. All the products have been synthesized in good to high yields and excellent diastereoselectivity by one-pot three-component 1,3-dipolar cycloaddition reactions of various derivatives of cyclopropene with azomethine ylides. Azomethine ylides were in situ generated from 11H-indeno[1,2-b]quinoxalin-11-one derivatives and amines, such as N-substituted and N-unsubstituted α-amino acids, benzylamines, and also peptides (dipeptide Gly-Gly and tripeptide Gly-Gly-Gly). To understand the mechanism that allows for azomethine ylide generation followed by 1,3-dipolar cycloaddition, a quantum chemical investigation was performed. The anticancer activity of some of the obtained compounds against the human leukemia K562 cell line was evaluated by flow cytometry in vitro.

中文翻译：

环丙烯的高非对映选择性一锅三组分1,3-偶极环加成反应与由11 H-茚并[1,2 - b ]-喹喔啉-11-酮生成的甲亚胺基团

已开发出一种简单有效的方法，用于合成具有螺稠合的11 H-茚并[1,2- b ]喹喔啉和环丙烷[ a ]吡咯嗪或氮杂双环[3.1.0]己烷部分的复杂化合物。通过环丙烯的各种衍生物与偶氮甲亚胺的一锅三组分1,3-偶极环加成反应可以高收率和高非对映选择性合成所有产物。甲亚胺叶立德是在原位从11产生ħ -茚并[1,2- b ]喹喔啉-11-酮衍生物和胺，如ñ -取代的和Ñ-未取代的α-氨基酸，苄胺以及肽（二肽Gly-Gly和三肽Gly-Gly-Gly）。为了理解允许产生甲亚胺叶立德然后进行1，3-偶极环加成的机理，进行了量子化学研究。通过流式细胞术体外评价了某些化合物对人白血病K562细胞的抗癌活性。

更新日期：2017-11-09

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