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

Adib, Mehdi; Peytam, Fariba; Rahmanian-Jazi, Mahmoud; Bijanzadeh, Hamid Reza; Amanlou, Massoud

doi:10.1016/j.tet.2017.09.042

Cited by 18 publications

(14 citation statements)

References 75 publications

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“…In a similar fashion, Adib and coworkers [115] described the synthesis of 1 H ‐imidazoles and 5 H ‐pyrrolo[1,2‐c]imidazoles from α‐azidochalcones. In this synthesis, α‐azidochalcones react with N , N , N ’, N ’‐tetramethyl guanidine to furnish 1 H ‐imidazoles through Michael addition‐cyclization.…”

Section: Different α‐Substituted Chalconesmentioning

confidence: 98%

α‐Substituted Chalcones: A Key Review

Al-Rifai

Mubarak

2021

ChemistrySelect

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Chalcones are attractive chemical motifs with various biological activities. Aryl substituted chalcones have been extensively studied and reviewed through the years. However, α‐substituted chalcones have rarely been investigated. Hence, this review highlights the α‐substituted chalcones: their synthetic routes, reported biological activities, and transformations to other organic compounds. To the best of our knowledge, this would be the first comprehensive review about α‐substituted chalcones. α‐Substitution of chalcones represents a promising approach to tune their reactivity since it has a direct influence on their activity as Michael acceptors. Additionally, α‐substitution has its effect on the structure and conformation of chalcones. Altering the reactivity of chalcones by α‐substitution has a great impact on their biological activity.

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Section: Different α‐Substituted Chalconesmentioning

confidence: 98%

α‐Substituted Chalcones: A Key Review

Al-Rifai

Mubarak

2021

ChemistrySelect

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“…Adib et al demonstrated the efficient synthesis of 2,4,5trisubstituted 1H-imidazoles 152 by coupling α-azidovinylketones and N,N,N',N'-tetramethylguanidine (Scheme 31). [62] The reaction proceeded via Michael addition of N,N,N',N' Handlon and his group reported a rapid construction of 2aminoimidazoles 156 via thermal or photo-induced cyclization of α-azidovinylesters with cyanamide in presence of potassium acetate (Scheme 32). [63] This reaction is an improved version of the method reported by Yu et al [57] who synthesized the same imidazole by heating α-azidovinylesters with cyanamide in the presence of 1 equiv.…”

Section: Pyrazolesmentioning

confidence: 99%

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Maurya

Borkotoky

2022

Asian J Org Chem

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Organic azides have been proven to possess versatile reactivity that is utilized to synthesize a large number of molecular scaffolds. Among the azides, α‐azidoketones and esters have been widely explored to synthesize numerous high valued N‐heterocycles. The enhanced acidity of the methylene hydrogen atoms by adjacent carbonyl or ester groups of α‐azidoketones and esters largely attributes to their unique chemical behaviour. It has been mostly utilized in two ways: a) the azides have been directly treated with other reagents in a basic medium and b) they are converted into α‐azidovinylketones and esters through Knoevenagel condensation with aldehydes and subsequently treated with various reagents to access nitrogen heterocycles. This review provides a general outlook and concise report on α‐azidoketones and esters towards the synthesis of various N‐heterocycles such as pyrroles, indoles, pyrazoles, imidazoles, triazoles, pyridines, pyrimidine, pyrazine and many others.

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“…In this paper, an e cient, facile synthetic approach including Michael-addition-cyclization of 2aminobenzimidazole 1 with α-azidochalcone 2 has been applied to obtain a library of 3-amino-2,4diarylbenzo [4,5]imidazo[1,2-a]pyrimidines 3a-ag. It is worth mentioning that over recent decade, α-azidochalcones 2 have been widely utilized to synthesize several aza-heterocycles [54][55][56][57][58][59][60][61][62][63][64][65][66] . To probe the generality of the proposed reaction, a mixture of 2-aminobenzimidazoles 1a,b, α-azidochalcones 2a-m (with electron-donating alkyl or methoxy groups as well as electron-withdrawing chlorine or bromine substituted phenyl, and heteroaryl substituents), and Et 3 N in EtOH were heated under the re ux conditions for 2h.…”

Section: Chemistrymentioning

confidence: 99%

Design, Synthesis, Molecular Docking, and Kinetic Study of 3-Amino-2,4-Diarylbenzo[4,5]Imidazo[1,2-a]Pyrimidines as Novel, Potent Α-Glucosidase Inhibitor

Peytam

Takalloobanafshi

Saadattalab

et al. 2021

Preprint

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In an attempt to find novel, potent α-glucosidase inhibitors, a library of poly-substituted 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines 3a-ag have been synthesized through heating a mixture of 2-aminobenzimidazoles 1 and α-azidochalcone 2 under the mild conditions. This efficient, facile protocol has been resulted into the desirable compounds with a wide substrate scope in good to excellent yields. Afterwards, their α-glucosidase inhibitory activities were investigated. Showing IC50 values ranging from 16.4 ± 0.36 µM to 297.0 ± 1.2 µM confirmed their excellent potency to inhibit α-glucosidase which may provide new drug candidates in the treatment of type II diabetes mellitus. Among various synthesized 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines, compound 3k exhibited the highest potency against α-glucosidase (IC50 = 16.4 ± 0.36 μM) which was 45.7 times more potent than acarbose as standard inhibitor (IC50 = 750.0 ± 1.5 μM). Moreover, the role of amine moiety on the observed activity was studied through substituting with chlorine and hydrogen resulted into a considerable deterioration on the inhibitory activity. Kinetic study and molecular docking study have confirmed the in-vitro results.

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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

Cited by 18 publications

References 75 publications

α‐Substituted Chalcones: A Key Review

α‐Substituted Chalcones: A Key Review

Recent Advances onα‐Azidoketones and Esters in the Synthesis ofN‐Heterocycles

Design, Synthesis, Molecular Docking, and Kinetic Study of 3-Amino-2,4-Diarylbenzo[4,5]Imidazo[1,2-a]Pyrimidines as Novel, Potent Α-Glucosidase Inhibitor

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