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

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

Show Affiliations

1. School of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
2. Department of Biophysics, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran
3. Department of Medicinal Chemistry, Drug Design and Development Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

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

Style	Citing Format
MLA	Adib M, et al.. "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." Tetrahedron, vol. 73, no. 48, 2017, pp. 6696-6705.
APA	Adib M, Peytam F, Rahmanianjazi M, Bijanzadeh HR, Amanlou M (2017). 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. Tetrahedron, 73(48), 6696-6705.
Chicago	Adib M, Peytam F, Rahmanianjazi M, Bijanzadeh HR, Amanlou M. "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." Tetrahedron 73, no. 48 (2017): 6696-6705.
Harvard	Adib M et al. (2017) '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', Tetrahedron, 73(48), pp. 6696-6705.
Vancouver	Adib M, Peytam F, Rahmanianjazi M, Bijanzadeh HR, Amanlou M. 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. Tetrahedron. 2017;73(48):6696-6705.
BibTex	@article{ author = {Adib M and Peytam F and Rahmanianjazi M and Bijanzadeh HR and Amanlou M}, title = {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}, journal = {Tetrahedron}, volume = {73}, number = {48}, pages = {6696-6705}, year = {2017} }
RIS	TY - JOUR AU - Adib M AU - Peytam F AU - Rahmanianjazi M AU - Bijanzadeh HR AU - Amanlou M TI - 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 JO - Tetrahedron VL - 73 IS - 48 SP - 6696 EP - 6705 PY - 2017 ER -

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