A new synthetic protocol that combines the advantages offered by eco-friendly solvent-free reactions and sequential transformations is reported. This strategy offers straightforward access to benzo[c]chromenes and benzo[b]furans from commercially available starting materials. This two-step, one-pot strategy consists of an Au-catalyzed hydrophenoxylation process followed by Pd-catalyzed C-H activation or Mizoroki-Heck reactions. The selectivity of the process towards C-H activation or Mizoroki-Heck reaction can be easily tuned.
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http://dx.doi.org/10.1002/chem.201404630 | DOI Listing |
J Org Chem
January 2025
Applied Organic Chemistry Group, Chemical Science and Technology Division, CSIR-North East Institute of Science and Technology, Jorhat 785006, India.
A synthetic strategy of a palladium-catalyzed cascade annulation reaction followed by aerial oxidation was designed to construct 6-benzo[c]chromene scaffolds. Various 6-benzo[c]chromenes were synthesized under mild reaction conditions using easily accessible -QMs and commercially available -hydroxyarylboronic acids. One of the synthesized chromenes has been ambiguously confirmed by single-crystal XRD analysis.
View Article and Find Full Text PDFOrg Lett
February 2024
Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100, Russia.
The action of 2-(1-arylethylidene)malononitriles on 2-nitro-1-benzo[]chromenes in the presence of EtN and MoO·2HO results in naphtho[2,1-]furans containing an allylidenemalononitrile unit in the α-position. The reaction proceeds with contraction of the pyran ring via a cascade carba-Michael addition/retro-oxa-Michael reaction/tautomerization/S2/oxidation process. In contrast, the reaction of 2-nitro-1-benzo[]chromenes with the cyclic Knoevenagel adduct derived from 1-indanone and malononitrile leads to dihydroindeno[1,2-]xanthenes.
View Article and Find Full Text PDFSci Rep
October 2023
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran.
In the research, the core-shell procedure synthesized a novel magnetically separable heterogeneous nanocatalyst with high stability named FeO@CPTMO@dithizone-Ni. In this method, FeO was modified as a magnetic core using surfactant (SDS) and polyethylene glycol (PEG) coating; after functionalizing the magnetic nanoparticles with 3-chloropropyl-tri-methoxysilane and dithizone, Ni metal was immobilized. The prepared catalyst was identified and specified utilizing diverse physicochemical techniques involving FT-IR, XRD, SEM, EMA, BET, ICP, EDS, TGA, Raman, and TEM.
View Article and Find Full Text PDFChem Commun (Camb)
September 2023
School of Pharmaceutical Sciences, South-Central Minzu University, Wuhan 430074, People's Republic of China.
A rhodium(III)-catalyzed redox-neutral spiroannulation approach to access the spiro[benzo[][1,4]oxazine-benzo[]chromene skeleton is described in this contribution. A variety of spiro[5.5]-heterocyclic scaffolds were obtained in moderate to excellent yields under mild conditions.
View Article and Find Full Text PDFChem Rec
December 2023
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering, Research Centre of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, P. R. China.
Organic cycles play an important role in chemistry, pharmacology and material science for their unique properties. Construction of organic cycles from thioalkynes attracted increasing attention due to the facile access of thioalkynes. 2H-Azirines were synthesized successfully from thioalkynyl oxime ethers.
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