An efficient method for the selective preparation of trifluoromethyl-substituted azepin-2-carboxylates and their phosphorous analogues has been developed via Cu(I)-catalyzed tandem amination/cyclization reaction of functionalized allenynes with primary and secondary amines.
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http://dx.doi.org/10.3390/molecules27165195 | DOI Listing |
RSC Adv
August 2023
College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University No. 26 Hexing Road Harbin 150040 P. R. China
Various multi-substituted pyrido[1,2-]pyrimidin-4-ones were synthesized a one-pot tandem CuI-catalyzed C-N bond formation/intramolecular amidation reaction at 130 °C in DMF. This protocol features simple operation, broad substrate scope, good functional group tolerance and gram scale preparation, thus allowing practical and modular synthesis of pyrido[1,2-]pyrimidin-4-ones from readily available 2-halopyridine and ()-3-amino-3-arylacrylate ester in good to excellent yields.
View Article and Find Full Text PDFJ Org Chem
January 2015
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China.
A CuI-catalyzed tandem reaction of 5-(2-bromoaryl)-N-aryl-1H-pyrazol-3-amines with active acetonitrile derivatives to prepare pyrazolo[5,1-a]isoquinolines in good to excellent yields has been successfully developed under mild conditions with heterocyclic ketene aminals (HKAs) as new ligands. This is the first time HKAs have been used as ligands for copper-catalyzed coupling reactions.
View Article and Find Full Text PDFChem Commun (Camb)
April 2013
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
A novel A21-CuI catalyzed direct nitrogenation of biphenyl halides for the direct synthesis of carbazoles via a direct C-H amination process has been developed. A recyclable and inexpensive Cu-catalyst was successfully employed in N-heterocyclic compound synthesis via tandem azidation and C-H amination, which makes this protocol very practical and easy to handle.
View Article and Find Full Text PDFJ Org Chem
February 2012
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226 001, India.
Several diversity-oriented syntheses of N-fused polycyclic heterocycles have been demonstrated but most of them are based on point diversity within the same library and usually involve time-consuming sequential multistep syntheses, which also suffer from low yields and/or poor precursor scopes. We have developed a new strategy for the syntheses of skeletal diverse N-fused polycyclic compounds via an Ugi-type MCR followed by a CuI-catalyzed coupling reaction or tandem Pictet-Spengler reaction. This two-step sequence provides eight distinct skeleton of fused {6-5-5-6}, {5-5-5-6}, {6-5-6-6}, and {5-5-6-6} ring systems that have applications in medicinal chemistry and chemical genetics too.
View Article and Find Full Text PDFJ Org Chem
August 2009
Johnson & Johnson Pharmaceutical Research & Development, LLC 3210 Merryfield Row, San Diego, California 92121, USA.
CuI/L5 (N,N'-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-amino-benzimidazoles through tandem aminations of 1,2-dihaloarenes in modest yields. This methodology is also applicable for the preparation of 1-H or 1-substutituted 2-aryl- or 2-alkyl-benzimidazoles.
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