A new one-pot preparation of polysubstituted imidazoles by a Staudinger/aza-Wittig/Ag(I)-catalyzed cyclization/isomerization has been developed. The easily accessible propargylazide derivatives reacted with triphenylphosphine, isocyanates, and amines sequentially to produce the fully substituted imidazoles in good overall yields in the presence of catalytic amount of AgNO/DMAP.
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http://dx.doi.org/10.1021/acs.joc.7b02606 | DOI Listing |
RSC Adv
September 2024
School of Chemical Sciences, Punyashlok Ahilyadevi Holkar Solapur University Solapur 413255 Maharashtra India
A metal-free one-pot method is established for the synthesis of tetrasubstituted imidazoles from the reaction of arylmethylamines and 1,2-dicarbonyls/benzoin. The -α-C(sp)- bond functionalization of arylmethylamines using a catalytic amount of AcOH afforded polysubstituted imidazoles under aerobic conditions in significant yields of up to 95%.
View Article and Find Full Text PDFJ Org Chem
May 2024
State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
In this paper, we report an innovative method for synthesizing 1-benzyl-2,4-diarylimidazole utilizing 1-phenylethanone-2-(2-pyridinyl) hydrazine and benzylamine, catalyzed by an I/CuI system. This approach represents a significant departure from traditional methods for synthesizing polysubstituted imidazoles; it employs the I/CuI catalyst to replace rare metal catalysts, thereby achieving high yields of substitution products (≤85%). This method for the generation of 1,2,4-triimidazole derivatives is characterized by its exceptional chemical selectivity and extensive substrate compatibility.
View Article and Find Full Text PDFRSC Adv
April 2023
Department of Organic Chemistry, Faculty of Chemistry, University of Science, Vietnam National University Ho Chi Minh City 700000 Viet Nam
Deep eutectic solvents (DESs) act as both an organic solvent and a useful catalyst for organic synthesis reactions, especially the synthesis of heterocyclic compounds containing the element nitrogen. DESs exhibit many important properties namely large liquid fields, biodegradability, outstanding thermal stability, and moderate vapor pressure. Amorphous carbon-bearing sulfonic acid groups (AC-SOH) are one of the new-generation solid acids showing strong acid activity.
View Article and Find Full Text PDFSci Rep
November 2022
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran.
CrO nanoparticles were prepared using Zingiber officinal extract which were used as an efficient and reusable catalyst in the practical synthesis of polysubstituted imidazoles by means of a convenient reaction of aromatic aldehydes with ammonium acetate and benzil under microwave irradiation and HO as solvent. The structure of the compounds was studied by IR and H-NMR spectrum. The most important benefits of this process are operational simplicity, reasonable reaction times, and excellent yield of products.
View Article and Find Full Text PDFOrg Lett
August 2022
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh 208 016, India.
An enantioselective (3+2) cycloaddition reaction of iminoesters occurring with opposite regioselectivity is reported. This reaction provides chiral polysubstituted pyrrolidines with high enantioselectivities (up to 97%), diastereoselectivities (>20:1), and yields (up to 99%). Interestingly, changing the alpha-substituents of the iminoesters from an aryl to an aliphatic (benzyl) group or hydrogen resulted in the formation of normal (3+2) cycloaddition products, also in excellent enantioselectivities.
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