Bicyclic hydrazines undergo a facile palladium/iodine mediated stereoselective ring opening on reaction with organoboronic acids affording trans-3,4-disubstituted hydrazino cyclopentenes in good to excellent yield.
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http://dx.doi.org/10.1039/b607389a | DOI Listing |
J Org Chem
December 2024
Pfizer Oncology Medicinal Chemistry, San Diego, California 92121, United States.
A 3-step modular procedure combining carboxylic acids with acyl hydrazines provides access to medicinally relevant [1,2,4]-fused triazoles. Good to excellent yields are achieved with tolerance of aliphatic and aryl substituents as well as 5-, 6-, and 7-membered rings for the fused ring. Conditions that can avoid column chromatography and be applicable for both small scale discovery efforts as well as large scale development processes are demonstrated within.
View Article and Find Full Text PDFChemistry
November 2024
Université Paris Cité, CNRS, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, F-75006, Paris, France.
This study presents efficient synthetic pathways for preparing novel azaspirocycles. These methodologies involve functionalizing key bicyclic hydrazines with a substituent on one of their bridgehead carbon atoms. The desired spirocyclic cores were successfully obtained through double reductive amination reactions, intramolecular cyclizations, and cleavages of the N-N bond.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Department of Chemistry and Chemical Biology, Cornell University, 122 Baker Laboratory, Ithaca, New York 14853, USA.
Materials formed by the ring-opening metathesis polymerization (ROMP) of cyclic olefins are highly valued for industrial and academic applications but are difficult to prepare free of metal contaminants. Here we describe a highly efficient metal-free ROMP of cyclobutenes using hydrazine catalysis. Reactions can be initiated via in situ condensation of a [2.
View Article and Find Full Text PDFBraz J Microbiol
June 2024
Departamento de Micologia, Universidade Federal de Pernambuco, Recife, Pernambuco, Brazil.
As the prevalence of drug-resistant Candida isolates continues to rise, the imperative for identifying novel compounds to enhance the arsenal of antifungal drugs becomes increasingly critical. Consequently, exploring new treatment strategies, including synthesizing molecular hybrids and applying combination therapy, is essential. For this reason, this study evaluated the efficacy of ten molecular hybrids of aza-bicyclic 2-isoxazoline-acylhydrazone belonging to two series 90 and 91 as possible anti-Candida agents.
View Article and Find Full Text PDFOrg Biomol Chem
May 2023
Université Paris Cité, CNRS, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, F-75006 Paris, France.
In recent years, spirocycles have been the focus of medicinal chemistry, and several drugs or drug candidates incorporating these "non-planar" chemical motifs have been developed. Herein, an unusual intramolecular Buchwald-Hartwig -arylation of bicyclic hydrazines is described. This key reaction gives access to various spiro[indoline-2,3'-piperidine] derivatives after reductive cleavage of a nitrogen-nitrogen bond.
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