An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.
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http://dx.doi.org/10.1021/acs.orglett.6b03433 | DOI Listing |
J Org Chem
July 2023
Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu 181143, Jammu and Kashmir, India.
An efficient, diversity-oriented synthesis of oxazepino[5,4-]quinazolin-9-ones, 6-chromeno[4,3-]quinolines, and dibenzo[,][1,6]naphthyridines was established involving a substrate-based approach under microwave-assisted and conventional heating conditions in high yields (up to 88%). The CuBr-catalyzed, chemoselective cascade annulation of -propargylated 2-hydroxybenzaldehydes and 2-aminobenzamides delivered oxazepino[5,4-]quinazolin-9-ones involving a 6-- cyclization-air oxidation-1,3-proton shift-7- cyclization sequence. This one-pot process showed excellent atom economy (-HO) and constructed two new heterocyclic rings (six- and seven-membered) and three new C-N bonds in a single synthetic operation.
View Article and Find Full Text PDFJ Org Chem
July 2022
Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu 181143, J&K, India.
A highly efficient microwave-assisted copper(II)-catalyzed cyclization cascade was established starting from readily accessible /-propargylated 2-hydroxy or 2-aminobenzaldehydes and -phenylenediamines to synthesize densely functionalized imidazo[1,2-][1,4]oxazepines and imidazo[1,2-][1,4]diazepines in high yields (up to 93%). This one-pot two-step process was found to be highly atom economical (-HO, -H) and operationally simple and enabled the generation of two new heterocycle rings (seven- and five-membered) and three new C-N bonds in a single synthetic operation. These reactions well tolerated a variety of substituents including electron-donating and electron-withdrawing groups and furnished the desired fused heterocycles in high yields under microwave irradiation in a very short reaction time.
View Article and Find Full Text PDFOrg Lett
July 2021
UMR CNRS 8038, Faculté de Pharmacie, Université de Paris, 4 avenue de l'Observatoire, 75270 Paris cedex 06, France.
Vibsatin A is a new neurotrophic vibsane-type diterpenoid comprising a bridged bicyclo[4.2.1]nonane skeleton.
View Article and Find Full Text PDFChemistry
June 2021
Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.
Virtually inert sulfur hexafluoride becomes a precious pentafluorosulfanylation agent, if properly activated by photoredox catalysis, to access α-fluoro and α-alkoxy SF -compounds. This advanced protocol converts SF in the presence of alkynols as bifunctional C-C- and C-O-bond forming reagents directly into pentafluorosulfanylated oxygen-containing heterocycles in a single step from α-substituted alkenes. The proposed mechanism is supported by theoretical calculations and gives insights not only in the pentafluorosulfanylation step but also into formation of the carbon-carbon bond and is in full agreement with Baldwin's cyclization rules.
View Article and Find Full Text PDFOrg Biomol Chem
March 2019
Division of Fluoro and Agrochemicals, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.
An efficient method was developed for the synthesis of substituted aryl-fused pyrazolooxazepines from ortho-O-propargyl aryl pyrazoles by gold catalysis. In this organic transformation a new C-N bond was formed regioselectively via 7-exo-dig cyclization. Moderate to good yields of aryl-fused pyrazolooxazepine derivatives were obtained with significant molecular complexity in one-pot.
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