Phenacyl azides as efficient intermediates: one-pot synthesis of pyrrolidines and imidazoles

Reddy, Chada Narsimha; Sathish, Manda; Adhikary, Susanta; Nanubolu, Jagadeesh Babu; Alarifi, Abdullah; Maurya, Ram Awatar; Kamal, Ähmed

doi:10.1039/c7ob00299h

Cited by 16 publications

(8 citation statements)

References 31 publications

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“…This last result is consistent with a synergistic cooperation of the basic ChCl/urea eutectic mixture [ 37 ] with Et 3 N in promoting the transformation at rt. α-Azido ketones are, indeed, known to be highly base sensitive and to undergo a base-promoted loss of nitrogen to form α-imino ketones upon protonation [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

Vitale

Cicco

Cellamare

et al. 2020

Beilstein J. Org. Chem.

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We report that phenacyl azides are key compounds for a regiodivergent synthesis of valuable, functionalized imidazole (32–98% yield) and pyrimidine derivatives (45–88% yield), with a broad substrate scope, when using deep eutectic solvents [choline chloride (ChCl)/glycerol (1:2 mol/mol) and ChCl/urea (1:2 mol/mol)] as environmentally benign and non-innocent reaction media, by modulating the temperature (25 or 80 °C) in the presence or absence of bases (Et3N).

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Section: Resultsmentioning

confidence: 99%

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

Vitale

Cicco

Cellamare

et al. 2020

Beilstein J. Org. Chem.

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“…Organic azides have attracted much attention since the first discovery of phenyl azides by Peter Grieb in 1864 Azides are valuable active intermediates, it can be easily transformed into triazoles, tetrazoles, amines, imines, isocyanates (Curtius rearrangement), and as the precursor of nitrene . Moreover, azides can also be used as pharmacophores, such as the HIV/AIDS drug zidovudine and novel azide‐functionalized Pt II complex picazoplatin …”

Section: Methodsmentioning

confidence: 99%

Azidative Aromatization of Quinone Methides Under Transition Metal and Solvent Free Conditions

Xiu

Song

et al. 2020

Eur J Org Chem

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Organic azides are synthetically and commercially useful intermediates with a wide variety of applications. In this work, azidative aromatization of quinone methides under transition metal and acid‐free conditions can avoid the forming of highly toxic and explosive hydrazoic acid and azide salts. The use of cesium carbonate as a catalyst and water as an effective additive, elimination of a transition metal catalyst, reaction solvent, and column chromatography separation led to an overall greener approach to access valuable benzyl azides in quantitative yields. Because the procedure can be used to prepare a serious of benzyl azides without contamination by any harmful transition metal residues, this new method has great potential in pharmaceutical synthesis and chemical biology studies.

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“…The deprotonated α ‐azidoketones readily eliminate a dinitrogen to generate N ‐unsubstituted imines 75 which can be utilized in many ways to synthesize desired molecules (Scheme 16). [46] These imines were reacted with cyclic amino acids to generate azomethine ylides 77 which underwent [3+2] cycloaddition with maleimides to yield diastereoselective pyrrolidines 73 .…”

Section: Five Membered N‐heterocycles From α‐Azidoketones/estersmentioning

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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Phenacyl azides as efficient intermediates: one-pot synthesis of pyrrolidines and imidazoles

Cited by 16 publications

References 31 publications

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

Azidative Aromatization of Quinone Methides Under Transition Metal and Solvent Free Conditions

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

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