Premium
One–pot synthesis of ethyl‐3‐aryl‐2‐(1 H ‐tetrazol‐5‐yl)acrylates and 3‐(1 H ‐tetrazol‐5‐yl)coumarins via tandem [2+3] dipolar cycloaddition reaction‐Knoevenagel condensation
Author(s) -
Jafari Chermahini Zahra,
Najafi Chermahini Alireza,
Dabbagh Hossein A.,
Teimouri Abbas
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201500026
Subject(s) - chemistry , sodium azide , salicylaldehyde , tetrazole , cycloaddition , aryl , dimethylformamide , tandem , yield (engineering) , cascade reaction , proton nmr , ammonium acetate , 1,3 dipolar cycloaddition , organic chemistry , azide , solvent , catalysis , stereochemistry , schiff base , alkyl , materials science , high performance liquid chromatography , metallurgy , composite material
A simple, one‐pot, three‐component, two‐step tandem method has been developed for the synthesis of ethyl‐3‐aryl‐2‐(1 H ‐tetrazol‐5‐yl)acrylates that may have biologically importance from ethyl cyanoacetate, sodium azide and a series of aromatic aldehydes with different substituents. Reactions were performed using ammonium chloride as the catalyst and dimethylformamide as the solvent. The results indicated that electron withdrawing groups in the phenyl ring leads to comparatively more yield. When we used the salicylaldehyde precursors, the corresponding coumarin derivatives containing tetrazole group were formed in good yields. All the synthesized compounds were fully characterized by 1 H, 13 C NMR, FT‐IR and mass spectroscopic techniques and elemental analysis. The obtained results rationalized by proposing a suitable mechanism. Efficient and simple reaction conditions, easy isolation process and very good yields are the advantages of this strategy for the synthesis of tetrazole compounds.