A Novel Base-Solvent Controlled Chemoselective Azide Attack on an Ester Group versus Keto in Alkyl 3-Substituted 3-Oxopropanoates: Mechanistic Insights

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作   者：

Nazariy T. Pokhodylo;  Olga Ya. Shyyka;  Vasyl S. Matiychuk; 

作者机构：

Prof. V. V. Pavlyuk Faculty of Chemistry Ivan Franko National University of Lviv Kyryla I Mefodiya;  79005;  Lviv;  Prof. M. D. Obushak;  6;  Ukraine; 

关键词：

1;  cyclocondensation;  2;  bketoesters;  3-triazoles;  azides;  chemoselectivity; 

期刊名称：

Chemistry Select

i s s n：

年卷期：

2017 年 2 卷 21 期

页   码：

5871-5876

页   码：

摘   要：

During the exploration of arylazides reactions with alkyl 3- substituted-3-oxopropanoates under the Dimroth reaction conditions (MeONa-MeOH) azide attack on ester group versus keto was found out in few examples yielding stable 3-alkyl-2- diazo-3-oxo-N-(aryl)propanamides instead of obvious target 1- aryl-5-alkyl-1H-1,2,3-triazole-4-carboxylic acids. The formation of diazocompounds was observed in case of 3-(4,4-diethoxymethyl)-, isopropyl-, cyclopropyl-3-oxopropanoate in the reaction with arylazides, especially, those containing electro-withdrawing substituents. Influence of the base-solvent system on diazo products yields was investigated and mechanistic insights of Dimroth reaction were discussed.