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A New Synthetic Strategy Towards 2,4,5-Trisubstituted 1H-Imidazoles and Highly Substituted Pyrrolo[1,2-C]Imidazoles by Use of Α-Azidochalcones Via Michael Addition-Cyclization Followed by Wittig Reaction Publisher



Adib M1 ; Peytam F1 ; Rahmanianjazi M1 ; Bijanzadeh HR2 ; Amanlou M3
Authors

Source: Tetrahedron Published:2017


Abstract

Efficient and facile protocols for the preparation of highly functionalized 1H-imidazoles and 5H-pyrrolo[1,2-c]imidazoles are described. Heating a mixture of an α-azidochalcones and N,N,N′,N′-tetramethyl guanidine under neat conditions gave the corresponding 2,4,5-trisubstituted 1H-imidazole via Michael addition-cyclization in excellent yields. Subsequently, the prepared 1H-imidazoles undergo addition-Wittig reaction with acetylenic esters in presence of triphenylphosphine in dichloromethane to afford 5H-pyrrolo[1,2-c]imidazoles in high yields. © 2017
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