We present the unprecedented reaction of a [3+3] cyclization of indol-2-yl carbinol with azadiene for the construction of a six-membered ring and the subsequent oxidative ring expansion reaction for the construction of indole azepinones.
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http://dx.doi.org/10.1039/c4cc04995k | DOI Listing |
Chem Commun (Camb)
September 2024
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. China.
The synthesis of tetraarylmethanes has long been a challenge in the field of synthetic chemistry. In this study, a series of tetraarylmethanes were successfully synthesized through the formal nucleophilic substitution reaction of indol-2-yl diaryl methanol catalyzed by Brønsted acid. The key success of this study lies in suppressing the influence of water molecules by forming hydrogen bonds with the TFE solvent.
View Article and Find Full Text PDFPhotochem Photobiol Sci
February 2023
Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Alcohol Clin Exp Res
February 2018
College of Pharmacy, Western University of Health Sciences, Pomona, California.
Background: Nociceptin/orphanin FQ, the endogenous peptide agonist for the opioid receptor-like receptor (also known as NOP or the nociceptin receptor), has been shown to block the acquisition and expression of ethanol (EtOH)-induced conditioned place preference (CPP). Here, we report the characterization of a novel small-molecule NOP ligand AT-312 (1-(1-((cis)-4-isopropylcyclohexyl)piperidin-4-yl)-1H-indol-2-yl)methanol) in receptor binding and GTPγS functional assays in vitro. We then investigated the effect of AT-312 on the rewarding action of EtOH in mice using the CPP paradigm.
View Article and Find Full Text PDFChem Commun (Camb)
July 2015
Key Lab of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, 5625 Renmin Street, Changchun 130022, China.
The chiral phosphoramide-catalyzed asymmetric reaction of indol-2-yl carbinols with enamides is presented. The method provided an efficient and novel way for the synthesis of chiral 2-indole-substituted 1,1-diarylalkane derivatives.
View Article and Find Full Text PDFOrg Lett
February 2015
Key Lab of Synthetic Rubber, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences , 5625 Renmin Street, Changchun 130022, China.
The synthesis of a pentacyclic indole compound corresponding to the core structure of the misassigned indole alkaloid, tronoharine (1), is presented. The key reactions were a formal [3 + 3] cycloaddition of an indol-2-yl carbinol with an azadiene for the construction of the 6/5/6/6 tetracyclic system containing an all-carbon quaternary center and an intramolecular substitution reaction of an amine and a triflate for the creation of the bridged azepine ring. In addition, some other interesting transformations discovered during the synthetic studies are also discussed.
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