Abstract
The 2,3-dihydro-1,4-benzodioxin structure is present in compounds having some interesting biological properties. The first access to this structure, performed from 2-alkyl-1,4-benzodioxin or benzene-1,2-diol via stoechiometric cyclization, generally gave mixtures of products. Recently, the organometallic-catalyzed synthesis of this structure was performed using mercuric oxide, or more interesting, palladium as the catalyst. The palladiumcatalyzed heteroannulation of various monoprop-2-ynylated catechol and aryl iodides in the presence of PdCl2(PPh3)2 and CuI afforded the corresponding 1-alkylidene or 1-arylidene-2,3-dihydro-1,4-benzodioxins in excellent chemical yields. However the palladium-catalyzed cyclisation of substituted benzene-1,2-diols with different propargylic carbonates gave the corresponding 1-alkylidene or 1-arylidene-2,3-dihydro-1,4-benzodioxins eventually substituted at position 2 by an aryl or an alkyl group. Moreover, this later methodology seems very powerful since it is possible to perform this heteroannulation in an asymmetric way in order to obtain the 1-alkyl- 2-alkylidene-2,3-dihydro-1,4-benzodioxins in enantioselectivities up to 96%.
Keywords: eusiderin, eusideroxylon zwageri, sinaiticin, analgesic, 1,4-benzodioxan, diels-alder reaction, condensation
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
2