Methods for the cyclodehydration of N-(aminoalkyl)benzamides are few and employ harsh reaction conditions. We have found that the easily prepared phosphonium anhydrides 1 (Hendrickson reagent) or 2 can be used for cyclodehydration of N-(aminoalkyl)benzamides under very mild conditions (room temperature) to produce five-, six-, and seven-membered cyclic amidines. Good yields are obtained by employing a temporary trityl group protection strategy. Cyclic analogue 2 can be used when the product cyclic amidine is organic-soluble, thus producing water-soluble byproducts.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo401082q | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of indole-fused benzodiazepine derivatives by photocatalyzed cascade reaction.
Chem Commun (Camb)
January 2025
Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
We report a cascade synthesis of indole-fused benzodiazepines by the photocatalyzed addition of phenacyl radical, generated from α-acetoxy acetophenone, to 2-(3-methyl-1-indol-1-yl)aniline, and subsequent cyclodehydration. A range of indole-fused benzodiazepines were obtained from readily available substrates.
View Article and Find Full Text PDFSynthesis of Oxabicyclo[3.2.1]octan-3-ol Scaffold via Burgess Reagent Mediated Cyclodehydration of δ-Diols under Acidic Conditions.
Org Lett
January 2025
Department of Chemistry, Department of Molecular Biosciences, Chemistry of Life Processes Institute, Center for Developmental Therapeutics, Northwestern University, Evanston, Illinois 60208-3113, United States.
Dehydrative cyclization of δ-diols was achieved by using the Burgess reagent under mild conditions to furnish a novel oxabicyclo[3.2.1]octan-3-ol scaffold.
View Article and Find Full Text PDFCuracozole is representative of a cyanobactin-like sub-family of ribosomally synthesized and post-translationally modified peptides (RiPPs). The molecule is distinguished by its small macrocyclic structure, a poly-azole sequence that includes a phenyloxazole moiety, and a d--Ile residue. The enzymatic steps required for its formation are not well understood.
View Article and Find Full Text PDFSynthesis of Hydrazonyl Sultones via Phosphine-Mediated Cyclodehydration of Vicinal Sulfo-acyl Hydrazides.
Org Lett
October 2024
Department of Chemistry, State University of New York at Buffalo, Buffalo, New York 14260-3000, United States.
We report a phosphine-mediated cyclodehydration procedure for the facile synthesis of -aryl/alkyl-substituted hydrazonyl sultones, a class of bioorthogonal reagents, from the readily prepared vicinal sulfo-acyl hydrazides in moderate to good yields. The aqueous stability and bioorthogonal reactivity of these hydrazonyl sultones toward bicyclo[6.1.
View Article and Find Full Text PDFMolecular structure and composition elucidation of an industrial humin and its fractions.
Green Chem
July 2024
Inorganic Chemistry and Catalysis, Institute for Sustainable and Circular Chemistry and Debye Institute for Nanomaterials Science, Faculty of Science, Utrecht University Universiteitsweg 99 3584 CG Utrecht The Netherlands
Humins, (side-)products of the acid-catalysed dehydration of carbohydrates, will be produced in substantial quantities with the development of industrial biorefining processes. Most structural knowledge about such humins is based on synthetic model humins prepared at lab-scale from typical carbohydrate(-derived) compounds. Here, we report the first extensive characterisation study of an industrial humin.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!