Unsaturated acyloxy sulfones 3 undergo intramolecular cyclization upon deprotonation with LHMDS in THF. Dehydration and double bond isomerization of the products upon exposure to acid, gave the fused ring furans, 4, in good yields. This strategy could be readily adapted to 12 from the cyclization reactions of acyloxy sulfones 11 prepared from phenols. Finally, this approach could be successfully modified to access dihydropyrans and benzopyrans.
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3126094 | PMC |
http://dx.doi.org/10.1016/j.tetlet.2011.03.120 | DOI Listing |
Chem Pharm Bull (Tokyo)
January 2025
Graduate School of Integrated Basic Sciences, Nihon University, 3-25-40 Sakurajosui, Setagaya-ku, Tokyo 156-8550, Japan.
A method for preparing the fused cyclohexane and pyrrolidine portion of the strychnos skeleton has been developed using domino intermolecular and intramolecular S2 cyclization. Using this method, the formation of pyrrolidine proceeded smoothly with good yield without the E2 elimination product. This reaction condition is effective for synthesizing the fused cyclohexane and pyrrolidine portion of the strychnos skeleton.
View Article and Find Full Text PDFPolymers (Basel)
January 2025
Mitsubishi Gas Chemical Company, Inc., Tokyo 100-8324, Japan.
Transparent X-ray shielding polymer films were developed by bulk photo copolymerization of in situ prepared bismuth carboxylate prepolymers with polymerizable exomethylene moieties and ,-dimethylacrylamide (DMAA). The bismuth-containing prepolymers were prepared via the polycondensation of BiPh, 2-octenylsuccinic acid (OSA), and itaconic acid (IA) bearing an exomethylene group for polymerization. OSA was a chain extender by intermolecular condensation and a stopper by intramolecular cyclization to inhibit cross-linkage.
View Article and Find Full Text PDFMolecules
January 2025
Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada.
A concise, transition metal-free four-step synthetic pathway has been developed for the synthesis of tetracyclic heterosteroidal compounds, 14-aza-12-oxasteroids, starting from readily available 2-naphthol analogues. After conversion of 2-naphthols to 2-naphthylamines by the Bucherer reaction, subsequent selective C-acetylation was achieved via the Sugasawa reaction and reduction of the acetyl group using borohydride, which resulted into the corresponding amino-alcohols. The naphthalene-based amino-alcohols underwent double dehydrations and double intramolecular cyclization with oxo-acids leading to one-pot formation of a C-N bond, a C-O bond and an amide bond in tandem, to generate two additional rings completing the steroidal framework.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
The construction of complex molecules under metal-free conditions multiple bond-forming steps in a cascade manner is highly desirable. Herein, we have developed an HFIP-alone promoted aminomethylation and intramolecular cyclization of allenamides, providing biologically relevant tetrahydro-β-carboline derivatives embedded with an allylic amine functionality. The metal-free protocol provided the desired tetrahydro-β-carboline derivatives under mild conditions.
View Article and Find Full Text PDFJ Am Soc Mass Spectrom
January 2025
Dipartimento di Scienze del Suolo, della Pianta e degli Alimenti, Università degli Studi di Bari Aldo Moro, Via G. Amendola 165/a, 70126 Bari, Italy.
Coenzyme Q (CoQ) and closely related compounds with varying isoprenoid tail lengths (CoQ, = 6-9) are biochemical cofactors involved in many physiological processes, playing important roles in cellular respiration and energy production. Liquid chromatography (LC) coupled with single or tandem mass spectrometry (MS) using electrospray (ESI) or atmospheric pressure chemical ionization (APCI) is considered the gold standard for the identification and quantification of CoQ in food and biological samples. However, the characteristic fragmentation exhibited by the CoQ radical anion ([M], / 862.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!