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. Issue 48 (30th November 2017)

• Record Type: Journal Article
• Authors: Adib, Mehdi; Peytam, Fariba; Rahmanian-Jazi, Mahmoud; Bijanzadeh, Hamid Reza; Amanlou, Massoud
• Is Part Of: Tetrahedron. Volume 73:Issue 48(2017)
• Page Start: 6696
• Page End: 6705
• Publication Date: 2017-11-30
• Subjects: α-Azidochalcones -- N, N, N′, N′-tetramethyl guanidine -- 2, 4, 5-Trisubstituted 1H-imidazoles -- 5H-pyrrolo[1, 2-c]imidazoles -- Michael addition-cyclization-Wittig reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.09.042
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Efficient and facile protocols for the preparation of highly functionalized 1 H -imidazoles and 5 H -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 1 H -imidazole via Michael addition-cyclization in excellent yields. Subsequently, the prepared 1 H -imidazoles undergo addition-Wittig reaction with acetylenic esters in presence of triphenylphosphine in dichloromethane to afford 5 H -pyrrolo[1, 2- c ]imidazoles in high yields. Graphical abstract: