Treatment of D-arabino-tetritol-1-yl-benzimidazole with P-toluenesulfonyl chloride (1molequiv) in pyridine, afforded the N-bridgehead heterocycles, 2R,3R,4S-trihydroxy-1:2:3:4-tetrahydropyridino[1,2-a]benzimidazole. The structure of the latter compound was determined by acylation, (1)H, and (13)C NMR spectroscopy and mass spectrometry.
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http://dx.doi.org/10.1016/j.carres.2007.10.010 | DOI Listing |
Antiinflamm Antiallergy Agents Med Chem
December 2024
Chemistry Department, Faculty of Science, The University of Jordan, Amman, 11942, Jordan.
Aims: This study aimed at the synthesis of several spiro[benzofuran-3,3'-pyrroles] derivatives by a three-component reaction conducted by mixing DMAD, N-bridgehead het-erocycles, and benzofuran-2,3-diones in dichloromethane at room temperature for 24 h. Moreover, in vitro evaluation of their cytotoxicity affinities against FMS-like tyrosine kinase 3 was carried out.
Objectives: The objective of this study was to use a one-pot, three-component reaction to synthesize a novel set of spiro[benzofuran-3,3'-pyrroles] derivatives.
Eur J Med Chem
June 2015
Neuroscience Medicinal Chemistry, Janssen Research & Development, Janssen-Cilag S.A., C/Jarama 75, 45007 Toledo, Spain. Electronic address:
The search for novel heterobicyclic compounds within the drug-like chemical space continues to be an area of interest in medicinal chemistry. Unsaturated N-bridgehead heterocycles are well represented in marketed drugs for a variety of therapeutic areas, and continue to play an important role in central nervous system (CNS) drug discovery programs. Examples of medicinal chemistry strategies that make use of N-bridged 5,6-bicyclic pyridines are discussed here in this Minireview, which covers the literature from 2010 up to 2014.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
May 2014
Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Meilong Road No. 130, Shanghai, 200237 (China).
A convenient and efficient synthetic method has been developed to construct highly functionalized N-bridgehead azepine skeletons, which are of great importance in biological and pharmaceutical industry. The reaction proceeds through a rhodium(II) azavinyl carbene intermediate, which initiated the intramolecular C-H functionalization with pyrrolyl and indolyl rings. A variety of azepine derivatives were obtained in moderate to good yields under mild reaction conditions with high chemoselectivity.
View Article and Find Full Text PDFChemistry
March 2013
Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza, Spain.
Forging the lock that autolocks! Rh-NHC catalysts promote a new access to 4 H-quinolizine species from 2-vinylpyridine and terminal and internal alkynes through C-H activation and C-C coupling reactions (see figure). N-Bridgehead heterocycle formation is favored for internal- over terminal-substituted butadienylpyridine derivatives in a thermal 6π-electrocyclization process.
View Article and Find Full Text PDFJ Org Chem
November 2011
Department of Chemistry, Saint-Petersburg State University, 198504 St. Petersburg, Russia.
Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.
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