65193-48-8

Upstream product

• 53175-33-0 N-(2-furylmethyl)-N-(prop-2-en-1-yl)amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 617-89-0 furan-2-ylmethanamine 
• 98-00-0 (2-furyl)methyl alcohol 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 98-01-1 furfural 
• 69374-42-1 allyl-furfurylidene-amine 
• 106-95-6 allyl bromide 
• 121564-33-8 N-tosylfurfurylamine 

Relevant academic research and scientific papers

Hydrosilylation-Promoted Furan Diels-Alder Cycloadditions with Stereoselectivity Controlled by the Silyl Group

Herein we describe an unprecedented B(C6F5)3-catalyzed cascade reaction of N-allyl-N-furfurylamides involving an initial intramolecular furan Diels-Alder reaction and subsequent ether cleavage. The reaction has a broad substrate scope, even tolerating a trialkyl-substituted olefin as the dienophile, which has not previously been observed with conventional furan Diels-Alder reactions. In addition, the relative configuration of the product can be controlled by the choice of the silyl group: reactions involving Et3SiH and iPr3SiH gave different diastereomers. Control experiments and the computational studies revealed that the steric bulk of the silyl group plays a key role in determining the reaction pathway and thus the relative configuration of the product.

Cascade of the Hinsberg / IMDAF reactions in the synthesis 2-arylsulfonyl-3a,6-epoxyisoindoles and 4a,7-epoxyisoquinolines in water

N-Furfuryl allylamines, readily accessible from corresponding furfurals or furfuryl amines, react with a broad range of arylsulfonyl chlorides with the formation of a 3a,6-epoxyisoindole core in one synthetic stage. Usually, in boiling water, the interaction sequence involves two consecutive steps: the Hinsberg reaction and the intramolecular Diels–Alder furanе (IMDAF) reaction. The scope and limitations of the proposed method were thoroughly investigated, and it was revealed that the key [4 + 2] cycloaddition step proceeds through an exo-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. The method allows the ability to obtain N-sulfaryl-substituted 3a,6-epoxyisoindoles and 4a,7-epoxyisoquinolines, which are potentially useful substrates for further transformations and subsequent bioscreening, in particular antimicrobial activity.

Intramolecular (4?+?3) cycloadditions of nitrogen-tethered epoxy enosilanes for the synthesis of heteropolycycles

Furans bearing epoxy enolsilane units via a tether that incorporates a nitrogen heteroatom, undergo intramolecular (4 + 3) cycloadditions to generate bis-heteroatomic polycyclic adducts having piperidine moieties in their frameworks. The cycloadducts, ultimately derived from furfural, a renewal chemical feedstock, are obtained with up to 4:1 dr and with ee retained from the epoxide.

Ring-rearrangement metathesis (RRM) mediated by ruthenium-indenylidene complexes

Several ruthenium-indenylidene complexes bearing Nheterocyclic carbenes (NHCs) and phosphanes have been investigated for the ring rearrangement of cyclic compounds by alkene metathesis. These catalysts were found to promote efficiently such domino reactio

On the use of removable steric buttresses in cycloaddition reactions

Use of bulky protecting groups, such as the trityl group, can be utilised to encourage cycloaddition reactions that otherwise do not proceed. Thus N-allylfurfurylamines, bearing the appropriate N-protecting group, can thermally cyclise; subsequent removal